Dimethylacetamide → 4-Cyano-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

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Reaction Steps

A mixture of 4-bromo-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (124 mg, 0.33 mmole), tris(dibenzylideneacetone)dipalladium(0)(15 mg, 0.02 mmole), 1,1′-bis(diphenylphosphino)ferrocene (18 mg, 0.03 mmole), zinc cyanide (23 mg, 0.20 mmole) and zinc (3 mg, 0.04 mmole) in dimethylacetamide (0.65 ml) was stirred at 120° C. for 4 h and twenty minutes before it was cooled to room temperature, quenched with water, filtered. The filtrate was partitioned between chloroform/isopropanol (3:1) and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of methanol and dichloromethane to give the title compound as a white solid (41 mg). MS: (+) m/z 325.87 (M+1), MS: (−) m/z 324.00 (M−1),

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