Ammonium formate → HCID 67233024, compound

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Reaction Steps

A mixture of palladium on carbon (10%, 20 mg), ammonium formate (74.4 mg, 1.18 mmol), 4-bromo-2-(4-fluoro-phenyl)-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid butyl ester and 7-bromo-2-(4-fluoro-phenyl)-4-hydroxy-thieno[2,3-c]pyridine-5-carboxylic acid butyl ester (50 mg, 0.118 mmol), example 34-c, in ethyl acetate (1.5 mL) was refluxed for 2.5 h. The catalyst was filtered off and the resulting solution was concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-60% ethyl acetate in hexanes to produce 11.0 mg of 2-(4-fluoro-phenyl)-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid butyl ester and 10.0 mg of 2-(4-fluoro-phenyl)-4-hydroxy-thieno[2,3-c]pyridine-5-carboxylic acid butyl ester. MS for 2-(4-fluoro-phenyl)-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid butyl ester: (+) m/z 346.0 (M+1). MS for 2-(4-fluoro-phenyl)-4-hydroxy-thieno[2,3-c]pyridine-5-carboxylic acid butyl ester: (+) m/z 346.0 (M+1).

Provenance & Evidence