[DB] N-(4-'G'-2,5-Dimethoxyphenethyl)-2,2,2-trifluoroacetamide to 2-(4-'G'-2,5-Dimethoxyphen

Query Query F

O

F

H N

H 2N

F

1. Query

Results

Date

16 reactions in Reaxys

2018-07-18 06h:28m:05s (UTC)

O

O G O

G O

Search as: Product, As drawn, No mixtures ))

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F

O

F

H N

O

F

H 2N

O

OH O

O O

Cl

Rx-ID: 44025904 View in Reaxys 1/16 Yield

Conditions & References Reaction Steps: 2 1: sodium hydride / tetrahydrofuran / -10 °C 2: water; potassium hydroxide / methanol / 20 °C With water, sodium hydride, potassium hydroxide in tetrahydrofuran, methanol Leth-Petersen, Sebastian; Petersen, Ida N.; Jensen, Anders A.; Bundgaard, Christoffer; Bæk, Mathias; Kehler, Jan; Kristensen, Jesper L.; ACS Chemical Neuroscience; vol. 7; nb. 11; (2016); p. 1614 - 1619 View in Reaxys

F

O

F

O

H N

H 2N

F O

O

O

O

O

Rx-ID: 44025929 View in Reaxys 2/16 Yield

Conditions & References

62 %

With water, potassium hydroxide in methanol, T= 20 °C Leth-Petersen, Sebastian; Petersen, Ida N.; Jensen, Anders A.; Bundgaard, Christoffer; Bæk, Mathias; Kehler, Jan; Kristensen, Jesper L.; ACS Chemical Neuroscience; vol. 7; nb. 11; (2016); p. 1614 - 1619 View in Reaxys

F

O

F

H N

O

F

H 2N

O

O O

O O

Cl

Rx-ID: 44026147 View in Reaxys 3/16 Yield

Conditions & References Reaction Steps: 3 1: sodium tetrahydroborate / ethanol / 20 °C 2: sodium hydride / tetrahydrofuran / -10 °C 3: water; potassium hydroxide / methanol / 20 °C With sodium tetrahydroborate, water, sodium hydride, potassium hydroxide in tetrahydrofuran, methanol, ethanol Leth-Petersen, Sebastian; Petersen, Ida N.; Jensen, Anders A.; Bundgaard, Christoffer; Bæk, Mathias; Kehler, Jan; Kristensen, Jesper L.; ACS Chemical Neuroscience; vol. 7; nb. 11; (2016); p. 1614 - 1619 View in Reaxys

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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F F O F

O HN

H 2N

O

I O

I O

Rx-ID: 28933737 View in Reaxys 4/16 Yield

Conditions & References

97 %

With sodium hydroxide in methanol, Time= 2h, T= 40 °C , Inert atmosphere Trachsel, Daniel; Nichols, David E.; Kidd, Stephanie; Hadorn, Marcel; Baumberger, Franz; Chemistry and Biodiversity; vol. 6; nb. 5; (2009); p. 692 - 704 View in Reaxys F

F O F

O HN

H 2N

O

Cl

H

O

O

Rx-ID: 9428982 View in Reaxys 5/16 Yield

Conditions & References

0.44 g

Stage 1: With sodium hydroxide in methanol, Time= 4h Stage 2: With hydrogenchloride in diethyl ether Trachsel, Daniel; Helvetica Chimica Acta; vol. 86; nb. 8; (2003); p. 2754 - 2759 View in Reaxys

F F O F

O

HN

H 2N

O

Cl

I

H

O

O

Rx-ID: 14177775 View in Reaxys 6/16 Yield

Conditions & References Reaction Steps: 2 1.1: Pd(PPh3)4 / tetrahydrofuran 2.1: NaOH / methanol / 4 h 2.2: 0.44 g / HCl / diethyl ether With sodium hydroxide, tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran, methanol Trachsel, Daniel; Helvetica Chimica Acta; vol. 86; nb. 8; (2003); p. 2754 - 2759 View in Reaxys

Copyright Š 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Reaction Steps: 3 1.1: CuI; Et3N / PdCl2(PPh3)2 / tetrahydrofuran / 0.02 h / 20 °C 1.2: 97 percent / tetrahydrofuran / 1 h / 20 °C 2.1: 91 percent / Bu4NF / tetrahydrofuran / 2 h 3.1: NaOH / methanol / 4 h 3.2: 0.44 g / HCl / diethyl ether With sodium hydroxide, copper(l) iodide, tetrabutyl ammonium fluoride, triethylamine, bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran, methanol, 1.2: Shonogashira coupling Trachsel, Daniel; Helvetica Chimica Acta; vol. 86; nb. 8; (2003); p. 2754 - 2759 View in Reaxys

O

F

F

O

H N

H 2N

F

Cl

O

O

Si

H

O

Rx-ID: 14202323 View in Reaxys 7/16 Yield

Conditions & References Reaction Steps: 2 1.1: 91 percent / Bu4NF / tetrahydrofuran / 2 h 2.1: NaOH / methanol / 4 h 2.2: 0.44 g / HCl / diethyl ether With sodium hydroxide, tetrabutyl ammonium fluoride in tetrahydrofuran, methanol Trachsel, Daniel; Helvetica Chimica Acta; vol. 86; nb. 8; (2003); p. 2754 - 2759 View in Reaxys

O

F

F

O

H N

H 2N

F O

O

O

Rx-ID: 8723611 View in Reaxys 8/16 Yield

Conditions & References With sodium hydroxide in methanol, Time= 2h, Heating, Hydrolysis Dowd; Herrick-Davis; Egan; DuPre; Smith; Teitler; Glennon; Journal of Medicinal Chemistry; vol. 43; nb. 16; (2000); p.

3074 - 3084 View in Reaxys F

F O F

O

HN O

H 2N

O

O

Rx-ID: 8723876 View in Reaxys 9/16

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Yield

Conditions & References With sodium hydroxide in methanol, Time= 2h, Heating, Hydrolysis Dowd; Herrick-Davis; Egan; DuPre; Smith; Teitler; Glennon; Journal of Medicinal Chemistry; vol. 43; nb. 16; (2000); p.

3074 - 3084 View in Reaxys F

F O

O

F HN

H 2N

O

O

O

Rx-ID: 8725241 View in Reaxys 10/16 Yield

Conditions & References With sodium hydroxide in methanol, Time= 2h, Heating, Hydrolysis Dowd; Herrick-Davis; Egan; DuPre; Smith; Teitler; Glennon; Journal of Medicinal Chemistry; vol. 43; nb. 16; (2000); p.

3074 - 3084 View in Reaxys F

F O

O

F HN

H 2N O

O I O

Rx-ID: 15600493 View in Reaxys 11/16 Yield

Conditions & References Reaction Steps: 3 1: 65 percent / pyridine / 120 °C 2: 65 percent / H2 / 10 percent Pd/C / methanol / 4 h / 2068.59 Torr 3: 15 percent aq. NaOH / methanol / 2 h / Heating With pyridine, sodium hydroxide, hydrogen, 10 wt. % palladium on activated carbon in methanol, 1: Substitution / 2: Catalytic hydrogenation / 3: Hydrolysis Dowd; Herrick-Davis; Egan; DuPre; Smith; Teitler; Glennon; Journal of Medicinal Chemistry; vol. 43; nb. 16; (2000); p.

3074 - 3084 View in Reaxys

F

O

F

O

H N

H 2N

F O

O

O

O

Rx-ID: 15619426 View in Reaxys 12/16

Copyright Š 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Yield

Conditions & References Reaction Steps: 2 1: 79 percent / H2; AcOH; 70 percent HClO4 / 10 percent Pd/C / 6 h / 3102.89 Torr 2: 15 percent aq. NaOH / methanol / 2 h / Heating With sodium hydroxide, perchloric acid, hydrogen, acetic acid, 10 wt. % palladium on activated carbon in methanol, 1: Reduction / 2: Hydrolysis Dowd; Herrick-Davis; Egan; DuPre; Smith; Teitler; Glennon; Journal of Medicinal Chemistry; vol. 43; nb. 16; (2000); p.

3074 - 3084 View in Reaxys

F

O

O

F H N

H 2N

F O

O

O

O

Rx-ID: 15619955 View in Reaxys 13/16 Yield

Conditions & References Reaction Steps: 2 1: 43 percent / H2; AcOH; 70 percent HClO4 / 10 percent Pd/C / 6 h / 3102.89 Torr 2: 15 percent aq. NaOH / methanol / 2 h / Heating With sodium hydroxide, perchloric acid, hydrogen, acetic acid, 10 wt. % palladium on activated carbon in methanol, 1: Reduction / 2: Hydrolysis Dowd; Herrick-Davis; Egan; DuPre; Smith; Teitler; Glennon; Journal of Medicinal Chemistry; vol. 43; nb. 16; (2000); p.

3074 - 3084 View in Reaxys

F

O

F H N

O

F

H 2N

O

O

O

Rx-ID: 15620597 View in Reaxys 14/16 Yield

Conditions & References Reaction Steps: 2 1: 65 percent / H2 / 10 percent Pd/C / methanol / 4 h / 2068.59 Torr 2: 15 percent aq. NaOH / methanol / 2 h / Heating With sodium hydroxide, hydrogen, 10 wt. % palladium on activated carbon in methanol, 1: Catalytic hydrogenation / 2: Hydrolysis Dowd; Herrick-Davis; Egan; DuPre; Smith; Teitler; Glennon; Journal of Medicinal Chemistry; vol. 43; nb. 16; (2000); p.

3074 - 3084 View in Reaxys

Copyright Š 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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O

O F

H N

F

H 2N F

F

F

O F O

F

O

F

F

Rx-ID: 4101514 View in Reaxys 15/16 Yield

Conditions & References With potassium hydroxide in isopropyl alcohol, Time= 3h, Ambient temperature Nichols, David E.; Frescas, Stewart; Marona-Lewicka, Danuta; Huang, Xuemei; Roth, Bryan L.; et al.; Journal of Medicinal Chemistry; vol. 37; nb. 25; (1994); p. 4346 - 4351 View in Reaxys F

F O F

O HN

H 2N

O

F

I

O

F

F

O

Rx-ID: 18122669 View in Reaxys 16/16 Yield

Conditions & References Reaction Steps: 2 1: 1.) CuI, KF / 1.) DMF, 120 deg C, 2.) DMF, 120 deg C, 8 h 2: 2N KOH / propan-2-ol / 3 h / Ambient temperature With potassium fluoride, potassium hydroxide, copper(l) iodide in isopropyl alcohol Nichols, David E.; Frescas, Stewart; Marona-Lewicka, Danuta; Huang, Xuemei; Roth, Bryan L.; et al.; Journal of Medicinal Chemistry; vol. 37; nb. 25; (1994); p. 4346 - 4351 View in Reaxys

Copyright Š 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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