Dimethylacetamide → [(4-Cyano-7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carbonyl)-amino]-acetic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of [(4-bromo-7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carbonyl)-amino]-acetic acid (130 mg, 0.32 mmole), tris(dibenzylideneacetone)dipalladium(0)(15 mg, 0.02 mmole), 1,1′-bis(diphenylphosphino)ferrocene (18 mg, 0.04 mmole), zinc cyanide (23 mg, 0.19 mmole) and zinc (3 mg, 0.04 mmole) in dimethylacetamide (640 μl) was stirred at 120° C. for 3 h before it was cooled to room temperature, partitioned between ethyl acetate and 1N NaOH (50 ml). The aqueous layer was acidified with 5 N HCl (10 ml) to pH=2, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on a C18 column with a gradient of water and acetonitrile in formic acid to give the title compound as a yellow solid (46 mg). MS: (+) m/z 355.22 (M+1), MS: (−) m/z 353.18 (M−1).

Provenance & Evidence