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78790-83-7

Ethyl 3-aminothieno[2,3-c]pyridine-2-carboxylate synthesis

3synthesis methods
-

Yield:78790-83-7 67%

Reaction Conditions:

with sodium ethanolate in N,N-dimethyl-formamide; for 2 h;

Steps:

1.C

Step C: Preparation of ethyl 3-aminothieno[2,3-c]pyridine-2-carboxylate: 3-Bromoisonicotinonitrile (2000 mg, 10.93 mmol) was combined with ethyl 2-mercaptoacetate (1.205 mL, 10.93 mmol) in 50 mL DMF. Sodium ethanolate (4.080 mL, 10.93 mmol) was added, and the reaction mixture was stirred for 2 hours. The reaction mixture was transferred to separatory funnel, diluted with H2O, brine, NaHCO3 and extracted with EtOAc. The combined organic layers were combined, dried over Na2SO4, and concentrated to a yellow solid. LCMS confirmed desired product. The crude product was pre-adsorbed onto silica column and eluted with 1-5% MeOH/CH2Cl2 to provide 1.631 g (67%) of the desired product. MS(+) m/z=223.1.

References:

US2007/49603,2007,A1 Location in patent:Page/Page column 38; 27