1H-Indole-3-carbonyl chloride

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Substances (2)

Citations (39)

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References

1

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100%

With oxalyl dichloride; formamide in dichloromethane

T=20°C; 2 h;

Mason, Jeffrey J.; Bergman, Jan; Janosik, Tomasz

Journal of Natural Products, 2008 , vol. 71, # 8 p. 1447 - 1450 Title/Abstract

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100%

With thionyl chloride in benzene

2 h; Reflux; Hide Experimental Procedure

Universita Degli Studi Di Siena

Patent: US2009/238761 A1, 2009 ; Location in patent: Page/Page column 37 ; Title/Abstract

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1:

1H-Indole-3-carbonylchloride (40). To a solution of 1H-indole-3-carboxylic acid (39) (100.0 mg, 0.6 mmol) in benzene dry (2.0 mL), thionylchloride (130.0 μL, 1.80 mmol) was added and the mixture was heated to reflux for 120 min. The crude was washed with benzene (2.x.10 mL) and evaporated to give 40 in quantitative yield. 1H NMR, 200 MHz, (CDCl3) δ 10.85 (br s, 1H), 8.20 (m, 1H), 7.48 (m, 1H), 7.30 (m, 1H), 7.19 (m, 1H), 7.03 (m, 1H). Anal (C9H6ClNO) C, H, N. 100%

With thionyl chloride in dichloromethane; N,N-

Abuhaie, Cristina-Maria; Bîcu, Elena; Rigo, Benoît; Gautret, Philippe; Belei, Dalila; Farce, Amaury; Dubois, Joëlle; Ghinet, Alina

dimethyl-formamide

T=20°C; Inert atmosphere; Hide Experimental Procedure

Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 1 p. 147 - 152 Title/Abstract

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1H-Indole-3-carbonyl chloride (17)

General procedure: Under inert atmosphere, a mixture of carboxylic acid 6-12 (Scheme 1) (1 equiv), thionyl chloride (1.5 equiv) and DMF (3-5 drops) in dichloromethane was stirred at rt until the complete consumption of the carboxylic acid (1H NMR control). The pale yellow solution was concentrated in vacuo to give the crude acid chloride 13-19 (Scheme 1) as a yellow pale solid in quantitative yield and used without further purification in the condensation reaction with phenothiazine to provide compounds 20-26.1H NMR (CDCl3, 400MHz) δ (ppm) 7.30-7.35 (m, 2H, ArH), 7.47-7.51 (m, 1H, ArH),8.13 (d, J = 3.5 Hz, 1H, ArH), 8.31 (s, 1H, ArH), 8.80 (s large, 1H, NH).

99%

With thionyl chloride in benzene

2 h; Reflux;

Brindisi, Margherita; Butini, Stefania; Franceschini, Silvia; Brogi, Simone; Trotta, Francesco; Ros, Sindu; Cagnotto, Alfredo; Salmona, Mario; Casagni, Alice; Andreassi, Marco; Saponara, Simona; Gorelli, Beatrice; Weikop, Pia; Mikkelsen, Jens D.; Scheel-Kruger, Jorgen; Sandager-Nielsen, Karin; Novellino, Ettore; Campiani, Giuseppe; Gemma, Sandra

Journal of Medicinal Chemistry, 2014 , vol. 57, # 22 p. 9578 - 9597 Title/Abstract

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96%

With oxalyl dichloride in dichloromethane

3 h; Heating;

Hagiwara, Daijiro; Miyake, Hiroshi; Murano, Kenji; Morimoto, Hiroshi; Murai, Masako; et al.

Journal of Medicinal Chemistry, 1993 , vol. 36, # 16 p. 2266 - 2278 Title/Abstract

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With thionyl chloride

Doyle et al.

Journal of the Chemical Society, 1956 , p. 2853,2856 Full Text View citing articles Show Details

With thionyl chloride

0.5 h; Heating;

Caramella, P; Corsico, A. Coda; Corsaro, A; Del Monte, D.; Albini, F. Marinone

Tetrahedron, 1982 , vol. 38, # 1 p. 173 - 182 Title/Abstract

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With pyridine; oxalyl dichloride in tetrahydrofuran

T=0°C;

Wasserman, Harry H.; Ennis, David S.; Vu, Chi B.; Schulte, Gayle; Munk, Morton E.; et al.

Heterocycles, 1993 , vol. 35, # 2 p. 975 - 995 Title/Abstract

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With oxalyl dichloride; N,Ndimethyl-formamide in dichloromethane

1 h; Ambient temperature;

Oliver, J. E.; Waters, R. M.; Lusby, W. R.; Flippen-Anderson, J. L.

Journal of Heterocyclic Chemistry, 1991 , vol. 28, # 6 p. 1569 - 1572 Title/Abstract

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With oxalyl dichloride in dichloromethane; N,Ndimethyl-formamide

Gaster, Laramie M.; Joiner, Graham F.; King, Frank D.; Wyman, Paul A.; Sutton, Jonathan M.; et al.

Journal of Medicinal Chemistry, 1995 , vol. 38, # 24 p. 4760 - 4763 Title/Abstract

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With oxalyl dichloride; N,Ndimethyl-formamide in dichloromethane

2 h; Ambient temperature;

Wyman, Paul A.; Gaster, Laramie M.; King, Frank D.; Sutton, Jonathon M.; Ellis, Elizabeth S.; Wardle, Kay A.; Young, Timothy J.

Bioorganic and Medicinal Chemistry, 1996 , vol. 4, # 2 p. 255 - 261 Title/Abstract

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With phosphorus trichloride in acetonitrile; benzene

0.416667 h; Ambient temperature;

Kutschy, Peter; Dzurilla, Milan; Takasugi, Mitsuo; Sabova, Adriana

Collection of Czechoslovak Chemical Communications, 1999 , vol. 64, # 2 p. 348 - 362 Title/Abstract

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With thionyl chloride

T=20°C; Chlorination;

Pedras, M. Soledade C.; Khan, Abdul Q.

Phytochemistry, 2000 , vol. 53, # 1 p. 59 - 69 Title/Abstract

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With phosphorus pentachloride in dichloromethane

Varnavas, Antonio; Lassiani, Lucia; Valenta, Valentina; Berti, Federico; Mennuni, Laura; Makovec, Francesco

Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 5 p. 741 - 751 Title/Abstract

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With phosphorus trichloride in toluene; acetonitrile

T=20°C; 0.416667 h;

Zaletova, Janka; Dzurilla, Milan; Kutschy, Peter; Pazdera, Pavel; Kovacik, Vladimir; Aldoelfi, Juraj; Bekesova, Slavka

Collection of Czechoslovak Chemical Communications, 2004 , vol. 69, # 2 p. 453 - 460 Title/Abstract

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With thionyl chloride; N,Ndimethyl-formamide in tetrahydrofuran

T=20°C; 1 h;

Ludwig, Joachim; Lehr, Matthias

Synthetic Communications, 2004 , vol. 34, # 20 p. 3691 - 3695 Title/Abstract

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With thionyl chloride

T=0°C; 1.5 h;

Sears, R. Bryan; Carpenter, Russell A.; Whitlock, Christine R.

Molecules, 2005 , vol. 10, # 2 p. 488 - 491 Title/Abstract

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With oxalyl dichloride; N,Ndimethyl-formamide in dichloromethane

T=20°C; 3 h;

Janosik, Tomasz; Shirani, Hamid; Wahlstroem, Niklas; Malky, Ilham; Stensland, Birgitta; Bergman, Jan

Tetrahedron, 2006 , vol. 62, # 8 p. 1699 - 1707 Title/Abstract

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With oxalyl dichloride in tetrahydrofuran

T=20°C; 12 h;

Eggers, Mary E.; Jog, Parag V.; Bates, Dallas K.

Tetrahedron, 2007 , vol. 63, # 49 p. 12185 - 12194 Title/Abstract

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With oxalyl dichloride; N,Ndimethyl-formamide in dichloromethane

T=20°C; 2 h; Hide Experimental Procedure

BIO-MEDISINSK INNOVASJON AS; COCKBAIN, Julian

Patent: WO2007/7072 A1, 2007 ; Location in patent: Page/Page column 25-26 ; Title/Abstract

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12:

A suspension of indole-3-carboxylic acid (2.90 g, 18.0 mmol) in CH2Cl2 (75 ml) was treated with oxalyl chloride (1.84 ml, 20.7 mmol) and DMF (1 drop) and the mixture was stirred at room temperature for 2 h, then concentrated in vacuo to leave the acid chloride as a yellow solid. This was dissolved in a mixture of CH2CI2 (30 ml) and THF (10 ml) and added dropwise (30 min) to a stirred solution of 4- (4-hydroxymethyl-piperidin-l-yl) butyric acid 2, 2 , 2-trichloroethyl ester (from Example 11) (4.98 g, 15.0 mmol) and NEt3 (1.82 g, 18.0 mmol) in CH2Cl2 (30 ml) .

The reaction mixture was stirred at room temperature overnight, treated with an aqueous satd. NaCl solution (25 ml) and 10percent aqueous NaHCO3 solution (25 ml) . The organic layer was dried over Na2SO4, filtered and evaporated in vacuo to a brown viscous oil. The residue was separated with flash chromatography (SiO2, EtOAc) . The product was obtained as a pale yellow solid (1.83 g, 25.6percent). Conversion to the hydrochloride salt was effected using etheral HCl.1H-NMR (300 MHz, CDCl3) :δ 9.02 (br S, 1 H) , 8.22-8.18 (m,l H), 7.92 (d, 1 H), 7.48-7.41 (m, 1 H), 7.35-7.28 EPO <DP n="27"/>(m, 2 H), 4.77 (s, 2 H), 4.24 (d, 2 H) 3.03 (d, 2 H), 2.59-2.44 (q, 5 H), 2.13-1.85 (m, 7 H), 1.60-1.43 (m, 2 H)13C-EMR (75 MHz, CDCl3) : δ 171.7, 165.5, 136.2, 131.5, 125.7, 122.8, 121.7, 121.0, 111.7, 108.0, 94.8, 73.7, 67.9, 57.5, 53.1, 35.4, 31.7, 28.8, 21.8MS(ES) : 477.1 [M + H]+ With thionyl chloride in dichloromethane

T=60°C; 2 h; Hide Experimental Procedure

Kissei Pharmaceutical Co., Ltd.

Patent: EP1932833 A1, 2008 ; Location in patent: Page/Page column 12; 14 ; Title/Abstract

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3.3; 3.6:

3. Synthesis of XO-CH151; XO-CH151 was prepared by converting indole-3-caboxylic acid into an acid chloride, amidating it with aqueous ammonia and then, converting to a tetrazole in a similar manner to that of XO-CH150 (the following scheme).; 6. Synthesis of XO-CH151 XO-CH148; Indole-3-carboxylic acid (0.494 g, 3.07 mmol) was suspended in dichloromethane (10 mL), and to the suspension were added thionyl chloride (0.27 mL, 3. 7 mmol) and acetonitrile (5 mL). The mixture was stirred for an hour at 60°C, and to the reaction mixture was further added thionyl chloride (0.27 mL, 3.7 mmol). The mixture was stirred for an hour. After the solvent of the reaction mixture was evaporated to dryness, the residue was dissolved in acetonitrile (5 mL). To the solution was added 28percent aqueous ammonia (2 mL) in an ice-water bath, and the mixture was stirred for 30 minutes. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water (twice) and brine and dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and dried under reduced pressure to give XO-CH148 as a pale yellow solid (0.252 g, 51percent yield).

With thionyl chloride

0.5 h; Heating / reflux; Hide Experimental Procedure

Kadow, John F.; Xue, Qiufen May; Wang, Tao; Zhang, Zhongxing; Meanwell, Nicholas A.

Patent: US2003/236277 A1, 2003 ; Location in patent: Page 35-36 ; Title/Abstract

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14:EXAMPLE 14; 1H-Indole-3-carboxylic acid (1-benzoyl-pyrrolidin-3-yl)-methyl-amide

EXAMPLE 14 1H-Indole-3-carboxylic acid (1-benzoyl-pyrrolidin-3-yl)-methyl-amide The procedure is the same as the following one, which was described in Blair et. al. PCT WO 00/76521 indole 3-carboxylic acid, (2.0 g) was dissolved in 5 ml of SOCl2.The mixture was heated to reflux for 30 minutes.Removal of excess of SOCl2 under vaccum provided intermediate 9, indole 3-

carbonyl chloride, which was carried to the next step without further purification.

A mixture of indole 3-carbonyl chloride, intermediate 9 (50 mg), N-Benzoyl-3-methylamino-pyrrolidine, intermediate 10, (57 mg), pyridine (44 mg) in THF (5 ml) was stirred at room temperature for 10 hours.Solvents were removed under vaccum, and the residue was purified using a Shimadzu automated preparative HPLC System to give 78 mg of the compound of example 14, N-Benzoyl-3-[N-(indol-3-yl-carbonyl)-N-methyl]amino-pyrrolidine: MS m/z: (M+H)+ calcd for C21H19FN3O3: 348.17; found 348.22. HPLC retention time: 1.40 p minutes (column A).

With oxalyl dichloride; N,Ndimethyl-formamide in dichloromethane

T=20°C; 3 h; Inert atmosphere;

Linton, Elizabeth C.; Kozlowski, Marisa C.

Journal of the American Chemical Society, 2008 , vol. 130, # 48 p. 16162 - 16163 Title/Abstract

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With oxalyl dichloride

Inert atmosphere;

Blechy, Aurellen; Zard, Samir Z.

Organic Letters, 2009 , vol. 11, # 13 p. 2800 - 2803 Title/Abstract

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With oxalyl dichloride; N,Ndimethyl-formamide in dichloromethane

T=20°C; 2 h; Hide Experimental Procedure

BIO-MEDISINSK INNOVASJON AS

Patent: WO2005/61483 A2, 2005 ; Location in patent: Page/Page column 32 ; Title/Abstract

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3:

Example 3 Synthesis of lH-indole-3-carboxylic acid 1- [3- (2, 2, 2-trichloroethyl- ethoxycarbonyl)-propyl]-piperidine-4-ylmethyl ester A suspension of indole-3-carboxylic acid (2.90 g, 18.0 mmol) in CH2Cl2 (75 ml) was treated with oxalyl chloride (1.84 ml, 20.7 mmol) and DMF (1 drop) and the mixture stirred at room temperature for 2 h, then concentrated in vacuo to leave the acid chloride as a yellow solid. This was dissolved in a mixture of CH2C12 (30 ml) and THF (10 ml) and added dropwise (30 min) to a stirred solution of 4- (4-hydroxymethyl-piperidin-1yl) butyric acid 2,2, 2-trichloroethyl ester (from example 2) (4.98 g, 15.0 mmol) and NEt3 (1.82 g, 18.0 mmol) in CH2CI2 (30 ml). The reaction mixture was stirred at room temperature overnight, treated with an aqueous satd. NaCl solution (25 ml) and 10 percent aqueous NaHCO3 solution (25 ml). The organic layer was dried over Na2SO4, filtered and evaporated in vacuo to a brown viscous oil. The residue was separated with flash chromatography (SiOz, EtOAc). The product was obtained as a pale yellow solid (1.83 g, 25.6 percent). Conversion to the hydrochloride salt was effected using etheral HCI. 1H-NMR (300 MHz, CDCl3):No. 9.02 (br s, 1 H), 8.22-8. 18 (m, l H), 7.92 (d, 1 H), 7.48-7. 41 (m, 1 H), 7.35-7. 28 (m, 2 H), 4.77 (s, 2 H), 4.24 (d, 2 H) 3.03 (d, 2 H), 2.59-2. 44 (q, 5 H), 2.13-1. 85 (m, 7 H), 1.60-1. 43 (m, 2 H) 13C-NMR (75 MHz, CDCl3) : 5 171.7, 165.5, 136.2, 131.5, 125.7, 122.8, 121.7, 121.0, 111.7, 108.0, 94.8, 73.7, 67.9, 57.5, 53.1, 35.4, 31.7, 28.8, 21.8 MS (ES): 477.1 [M + H] + With oxalyl dichloride in 1,2-dichloro-ethane

T=0 - 20°C; 1 h; Hide Experimental Procedure

DAIICHI PHARMACEUTICAL CO., LTD.

Patent: EP1698611 A1, 2006 ; Location in patent: Page/Page column 39 ; Title/Abstract

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13:

Example 13 trans-4-((2S,4S)-1-{2,5-Dichloro-4-[(indol-3-yl)carboxamido]phenyl}acetyl-4-methoxypyrrolidin-2-yl)methoxycyclohexane-1-carboxylic acid ethyl ester (29) Oxalyl chloride (0.106 mL, 1.21 mmol) in 1,2-dichloroethane (3 mL) was added to indole-3-carboxylic acid (172 mg, 1.07 mmol) in 1,2-dichloroethane (3 mL) under stirring at 0°C. The reaction mixture was stirred for 1 hour at room temperature and concentrated to dryness under reduced pressure.

The residue was dissolved in 1,2-dichloroethane (3 mL), and the solution was added to trans-4-[(2S,4S)-1-(4-amino-2,5-dichlorophenyl)acetyl-4-methoxypyrrolidin-2-yl]methoxycyclohexane1-carboxylic acid ethyl ester (348 mg, 0.714 mmol) in 1,2-dichloroethane (15 mL) under stirring at 0°C. The reaction mixture was stirred for 10 hours under reflux conditions.

The reaction mixture was cooled to room temperature, and water (20 mL) was added thereto, followed by extraction with 1,2-dichloroethane.

The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to dryness under reduced pressure.

The residue was purified through silica gel column chromatography, and, from a fraction obtained through use of chloroform:ethyl acetate (9:1 to 3:1, v/v), the title compound (29) was obtained as a crystalline powder (340 mg, 76percent).

Melting point: 188-197°C. 1H-NMR(CDCl )δ: 1.21-1.31(5H,m), 1.44-1.51(2H,m), 1.97-2.36(7H,m), 3.27(1H,m), 3.34 and 3.36(3H,each s), 3.50-4.35(11H,series of m), 7.26-7.30(3H,m), 7.41(1H,m), 7.69(1H,m), 3 8.06(1H,m), 8.17(1H,m), 8.62(1H,m), 9.54(1H,m).

Element analysis: Calcd for C32H37Cl2N3O6: C, 60.95; H, 5.91; N,6.60.

Found: C,60.75; H,5.83; N,6.60.

With oxalyl dichloride; N,Ndimethyl-formamide in dichloromethane

T=20°C; 2 h;

Brudeli, Bjarne; Moltzau, Lise Roman; Andressen, Kjetil Wessel; Krobert, Kurt A.; Klaveness, Jo; Levy, Finn Olav

Bioorganic and Medicinal Chemistry, 2010 , vol. 18, # 24 p. 8600 - 8613 Title/Abstract

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With thionyl chloride; N,Ndimethyl-formamide in dichloromethane

T=0 - 20°C;

Von Reuss, Stephan H.; Bose, Neelanjan; Srinivasan, Jagan; Yim, Joshua J.; Judkins, Joshua C.; Sternberg, Paul W.; Schroeder, Frank C.

Journal of the American Chemical Society, 2012 , vol. 134, # 3 p. 1817 - 1824 Title/Abstract

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With oxalyl dichloride

T=50°C; 1 h; Inert atmosphere;

Vaillard, Victoria A.; Guastavino, Javier F.; Buden, Maria E.; Bardagi, Javier I.; Barolo, Silvia M.; Rossi, Roberto A.

Journal of Organic Chemistry, 2012 , vol. 77, # 3 p. 1507 - 1519 Title/Abstract

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With oxalyl dichloride in dichloromethane; N,Ndimethyl-formamide

T=0 - 23°C; 0.333333 h; Hide Experimental Procedure

BOYCE THOMPSON INSTITUTE FOR PLANT RESEARCH; CALIFORNIA INSTITUTE OF TECHNOLOGY; SCHROEDER, Frank, Clemens; VON REUSS, Stephan, Heinrich; CHOE, Andrea; STERNBERG, Paul, Warren

Patent: WO2013/22985 A2, 2013 ; Location in patent: Paragraph 0246 ; Title/Abstract

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18:

[0246] Next, a solution of indole-3-carbonyl chloride was prepared. A well-stirred suspension of indole-3-carboxylic acid (67.7 mg, 0.42 mmol) in dry DCM (2 ml) containing a small amount of dimethylformamide (DMF) (20 μί) was treated with oxalyl chloride (0.84 mmol, 107 mg, 72 μ ) at 0 °C. Following addition to the oxalyl chloride, the mixture was stirred for 20 minutes at 23 °C, producing a clear, slightly yellow solution. This solution was evaporated to dryness in vacuo at 0.1 Torr to ensure removal of excess oxalyl chloride, and was subsequently re-dissolved in 2 ml of dry DCM. With thionyl chloride in dichloromethane; N,Ndimethyl-formamide

T=20°C; Inert atmosphere; Hide Experimental Procedure

Ghinet, Alina; Moise, Iuliana-Monica; Rigo, Benoît; Homerin, Germain; Farce, Amaury; Dubois, Joëlle; Bîcu, Elena

Bioorganic and Medicinal Chemistry, 2016 , vol. 24, # 10 p. 2307 - 2317 Title/Abstract

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1:General procedure for the preparation of acid chlorides 32-42

General procedure: Under inert atmosphere, a mixture of carboxylic acid 21-31 ( Scheme 1 ) (1 equiv), thionyl chloride (1.5 equiv) and DMF (3-5 drops) in dichloromethane was stirred at rt until the complete consumption of the carboxylic acid (1H NMR control). The pale yellow solution was concentrated in vacuo to give the crude acid chloride 32-42 ( Scheme 1 ) as a yellow pale solid in quantitative yield With oxalyl dichloride; N,Ndimethyl-formamide in dichloromethane

T=0 - 20°C; 3 h;

Zhang, Lanlan; Geng, Yu; Jin, Zhong

Journal of Organic Chemistry, 2016 , vol. 81, # 9 p. 3542 - 3552 Title/Abstract

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With thionyl chloride in DME; dichloromethane

T=20°C; 2.16667 h;

Dong, Chuanfu; Dolke, Franziska; Von Reuss, Stephan H.

Organic and Biomolecular Chemistry, 2016 , vol. 14, # 30 p. 7217 - 7225 Title/Abstract

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With oxalyl dichloride; N,Ndimethyl-formamide in dichloromethane

T=20°C; 2 h; Hide Experimental Procedure

NATIONAL UNIVERSITY OF SINGAPORE; LEE, Sang Hyun; DYMOCK, Brian William; KITAGAWA, Mayumi; SEE, Cheng Shang

Patent: WO2016/200339 A1, 2016 ; Location in patent: Page/Page column 107-108 ; Title/Abstract

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29:Chemical Example 29 (Compound 29) ia2191 V-(isoquinolin-5-yl)-1H-indole-3-carboxamide

General procedure: General procedure (15): To a suspension of the carboxylic acid (1.0 equiv) in dichloromethane (10 mL for 0.838 mmol of starting material), oxalyl chloride 2.0 M solution in dichloromethane (approximately 1.5 mL) was added, followed by one drop of DMF. The reaction was stirred at room temperature for 2 h. The solution was evaporated under vacuum to afford the crude acid chloride. Dichloromethane was added to the crude acid chloride and evaporated under vacuum again for 2 times. The acid chloride was then re-dissolved in THF and added slowly to a solution of the amine derivative (1.2 equiv) and triethylamine (2.5 equiv) in THF. The reaction was stirred at room temperature for 16 h. The mixture was poured into water and extracted with ethyl acetate 3 times. The combined organic layer was washed with brine, dried over anhydrous sodium sulphate, concentrated in vacuo and purified by flash silica gel column chromatography to afford the amide product. Chemical Example 29 (Compound 29) ia2191 V-(isoquinolin-5-yl)-1H-indole-3-carboxamide Compound 29 [a219] (101 mg, 0.352 mmol) was prepared as a brown solid from 1/-/-indole- 3-carboxylic acid (135 mg, 0.838 mmol) and 5-aminoisoquinoline (145 mg, 1.006 mmol) according to general procedure (15) using 9:1 ethyl acetate/methanol as eluent for flash silica gel column chromatography and subsequent recrystallization from methanol. Yield: 42percent. 1H NMR (400 MHz, DMSO) δ: 11.80 (s, 1 H), 9.98 (s, 1 H), 9.35 (d, J = 0.7 Hz, 1 H), 8.53 (d, J = 6.0 Hz, 1 H), 8.44 (s, 1 H), 8.20 - 8.14 (m, 1 H), 7.99 (t, J = 7.0 Hz, 2H), 7.94 (d, J = 6.0 Hz, 1 H), 7.72 (t, J = 7.8 Hz, 1 H), 7.53 - 7.47 (m, 1 H), 7.22 - 7.13 (m, 2H). 13C NMR (100 MHz, DMSO) δ: 163.86, 152.45, 142.51 , 136.24, 133.55, 131.11 , 129.15, 128.87, 127.17, 126.48, 126.43, 124.59, 122.16, 121.02, 120.71 , 116.41 , 111.96, 109.97. LC-MS (ESI): m/z 288.1 [M + H]+.

2

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3

Multi-step reaction with 2 steps 1: 61 percent / aq. NaOH / propan-2-ol / 1 h / 85 - 90 °C 2: PCl3 / toluene; acetonitrile / 0.42 h / 20 °C View Scheme

Zaletova, Janka; Dzurilla, Milan; Kutschy, Peter; Pazdera, Pavel; Kovacik, Vladimir; Aldoelfi, Juraj; Bekesova, Slavka

Collection of Czechoslovak Chemical Communications, 2004 , vol. 69, # 2 p. 453 - 460 Title/Abstract

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in hexane; dichloromethane

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Donatsch; Peter; Engel; Gunter; Hugi; Bruno; Richardson; Brian P.; Stadler; Hildegard R.; Stadler; Brigitte M.; Stadler; Sigrid A.; Breuleux; Gerald

Patent: US4789673 A1, 1988 ; Title/Abstract

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A.1.a:(a)

(a) Indol-3-yl carboxylic acid chloride 32.2 g (0.2M) dry indol-3-yl carboxylic acid are suspended in 150 ml absolute methylene chloride. 26 ml (0.3M) oxalyl chloride are added to the stirred mixture at 20° C. over 30 minutes.

Gas evolution results.

The mixture is stirred for 31/2 hours at 20° C. 150 ml Hexane are added.

The mixture is stirred for another 20 minutes and the resultant heading compound filtered off, washed with methylene chloride/hexane 1:1 dried at 20° in a vacuum to give beige crystals, M.pt. 135°-136° (decomp) which are used further without purification.

in hexane; dichloromethane

Sandoz Ltd.

Patent: US4797406 A1, 1989 ;

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Title/Abstract

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1.a:(a)

(a) Indol-3-yl carboxylic acid chloride 32.2 g (0.2M) dry indol-3-yl carboxylic acid are suspended in 150 ml absolute methylene chloride.

26 ml oxalyl chloride are added to the stirred mixture at 20° C. over 30 minutes.

Gas evolution results.

The mixture is stirred for 31/2 hours at 20° C. 150 ml Hexane are added.

The mixture stirred for another 20 minutes and the resultant heading compound filtered off, washed with methylene chloride/hexane 1:1 dried at 20° in a vacuum to give beige crystals, M.pt.

135°-136° (decomp) which are used further without purification.

4

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in diethyl ether

T=0°C; 1 h;

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Hogan,I.T.; Sainsbury,M.

Tetrahedron, 1984 , vol. 40, p. 681 Full Text View citing articles Show Details

5

Synthesize Find similar Indol, Oxalsaeure-dichlorid, 2) Δ (115-120grad; neben einem Dimeren);

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WORMSER; ELKIN

Journal of pharmaceutical sciences, 1961 , vol. 50, p. 976 - 977 Title/Abstract

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6

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Journal of Organic Chemistry, 1958 , vol. 23, p. 303 Full Text View citing articles Show Details

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