(1H-indol-3-yl)(naphthalen-1-yl)methanone

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O HN

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6 reactions in Reaxys

2016-03-09 09h:33m:45s (EST)

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NH HN Cl

O

O

Rx-ID: 4605747 View in Reaxys 1/6 Yield 91 %

Conditions & References 1 :To a cooled solution of indole (5.85g, 50mmol) in ether (50ml) under nitrogen was added slowly a solution of methylmagnesium bromide (3M) in ether (17.5ml).

After addition, the reaction mixture was warmed up to room temperature and stirred for 2h at room temperature.

Then the mixture was cooled down again to 0°C, and to it was added slowly with stirring a solution of 1-naphthoylchloride (9.5g, 50mmol) in ether (50ml).

The resulting mixture was warmed up to room temperature and stirred for 2h at room temperature followed by slow addition of saturated ammonium chloride solution (375ml).

The mixture was then stirred overnight at room temperature.

A white solid was formed, filtered, washed by ether and dried under high vacuum to give 3-(1-naphthoyl)-1H-Indole 1 (12.3g, 91percent).

Stage 1: With methylmagnesium bromide in diethyl ether, Time= 2h, T= 20 °C , Inert atmosphere Stage 2: in diethyl ether, Time= 2h, T= 0 - 20 °C Stage 3: With ammonium chloride in diethyl ether, T= 20 °C Patent; Randox Laboratories Ltd.; EP2487155; (2012); (A1) English View in Reaxys With MeMgX in diethyl ether D'Ambra, Thomas E.; Eissenstat, Michael A.; Abt, Jeffrey; Ackerman, James H.; Bacon, Edward R.; Bell, Malcolm R.; Carabateas, Philip M.; Josef, Kurt A.; Kumar, Virendra; Weaver III, John D.; Arnold, Renee; Casiano, Frances M.; Chippari, Susan M.; Haycock, Dean A.; Kuster, Joan E.; Luttinger, Daniel A.; Stevenson, Joan I.; Ward, Susan J.; Hill, W. Adam; Khanolkar, Atmaram; Makriyannis, Alexandros; Bioorganic and Medicinal Chemistry Letters; vol. 6; nb. 1; (1996); p. 17 - 22 View in Reaxys 1 : Preparation of 3-(1-naphthoyl)-1H-indole 1 Example-1 Preparation of 3-(1-naphthoyl)-1H-indole 1 To a cooled solution of indole (5.85 g, 50 mmol) in ether (50 ml) under nitrogen was added slowly a solution of methylmagnesium bromide (3M) in ether (17.5 ml).

After addition, the reaction mixture was warmed up to room temperature and stirred for 2 h at room temperature.

Then the mixture was cooled down again to 0° C., and to it was added slowly with stirring a solution of 1-naphthoylchloride (9.5 g, 50 mmol) in ether (50 ml).

The resulting mixture was warmed up to room temperature and stirred for 2 h at room temperature followed by slow addition of saturated ammonium chloride solution (375 ml).

The mixture was then stirred overnight at room temperature.

A white solid was formed, filtered, washed by ether and dried under high vacuum to give 3-(1-naphthoyl)-1H-Indole 1 (12.3 g, 91percent).

With methylmagnesium bromide, ammonium chloride Patent; RANDOX LABORATORIES LIMITED; US2012/208213; (2012); (A1) English View in Reaxys With aluminum oxide in neat (no solvent), Time= 0.133333h, T= 100 °C , Microwave irradiation, Green chemistry Lai, Qiu Yu; Liao, Rong Su; Wu, Shao Yong; Zhang, Jia Xin; Duan, Xin Hong; New Journal of Chemistry; vol. 37; nb. 12; (2013); p. 4069 - 4076 View in Reaxys 1 : Example - 1: Example - 1:

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Preparation of 3-(1-naphthoyl)-1H-indole 1 To a cooled solution of indole (5.85g, 50mmol) in ether (50ml) under nitrogen was added slowly a solution of methylmagnesium bromide (3M) in ether (17.5ml).

After addition, the reaction mixture was warmed up to room temperature and stirred for 2h at room temperature.

Then the mixture was cooled down again to 0°C, and to it was added slowly with stirring a solution of 1-naphthoylchloride (9.5g, 50mmol) in ether (50ml).

The resulting mixture was warmed up to room temperature and stirred for 2h at room temperature followed by slow addition of saturated ammonium chloride solution (375ml).

The mixture was then stirred overnight at room temperature.

A white solid was formed, filtered, washed by ether and dried under high vacuum to give 3-(1-naphthoyl)-1H-Indole 1 (12.3g, 91percent).

With methylmagnesium bromide, ammonium chloride Patent; Randox Laboratories Ltd.; Fitzgerald, Stephen Peter; Innocenzi, Paul John; Lowry, Philip Andrew; McConnell, Ivan Robert; Benchikh, Elouard; EP2698385; (2014); (A1) English View in Reaxys

NH

O

O

NH NH

O

HN

HN

O

NH

HN

O

Rx-ID: 9767681 View in Reaxys 2/6 Yield

Conditions & References

38 %, 33 Stage 1: With sodium in tetrahydrofuran, T= 0 °C %, 11 %, 6 Stage 2: in tetrahydrofuran, Time= 2h, T= 0 - 5 °C % Banerji, Avijit; Bandyopadhyay, Debasish; Basak, Bidyut; Heterocycles; vol. 63; nb. 10; (2004); p. 2371 - 2377 View in Reaxys

O N O

HN S

NH 2

Rx-ID: 4418460 View in Reaxys 3/6 Yield

Conditions & References

48 %

in benzene, Time= 50h, Irradiation Oda, Kazuaki; Hiratsuka, Rin; Machida, Minoru; Heterocycles; vol. 43; nb. 2; (1996); p. 463 - 470 View in Reaxys

F O F N

F HN S

O

NH 2

Rx-ID: 4459774 View in Reaxys 4/6

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Yield

Conditions & References

53 %

in benzene, Time= 50h, Irradiation Oda, Kazuaki; Hiratsuka, Rin; Machida, Minoru; Heterocycles; vol. 43; nb. 2; (1996); p. 463 - 470 View in Reaxys

NH O

HN

Rx-ID: 44409 View in Reaxys 5/6 Yield

Conditions & References With diethyl ether, ethylmagnesium bromide, Erwaermen der Reaktionsloesung mit <1>Naphthoylchlorid Buu-Hoi et al.; Journal of the Chemical Society; (1957); p. 625,627 View in Reaxys

NH O HN

O

O

Rx-ID: 24909976 View in Reaxys 6/6 Yield

Conditions & References 2.C : Preparation 2C Preparation 2C Following a procedure similar to that described in Preparation 2A above, 30.7 g. (0.262 mole) of indole was reacted with 112.5 ml. of a 2.8 M solution of methyl magnesium bromide in MDC, and the resulting Grignard reagent was treated with a solution of 50 g. (0.26 mole) of 1-naphthoyl chloride in 50 ml. of MDC. There was thus obtained 57.3 g. of 3-(1-naphthylcarbonyl)indole as an oil.

Patent; Sterling Drug Inc.; US5068234; (1991); (A1) English View in Reaxys

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