Dimethylacetamide → HCID 68428506, compound

Participants

Reaction Steps

A solution of 4-bromo-2-tert-butyl-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (100 mg, 0.28 mmol), tris(dibenzylideneacetone)dipalladium(0)(13 mg, 0.014 mmol), 1,1′-bis(diphenylphosphino) ferrocene (15 mg, 0.028 mmol), zinc dust (2 mg, 0.033 mmol), and zinc cyanide (20 mg, 0.168 mmol) in 0.56 mL of dimethylacetamide was heated at 115° C. for 5 h under a nitrogen atmosphere. The mixture was cooled, diluted with ethyl acetate and saturated aqueous ammonium chloride and filtered through a celite pad. The organic fraction was isolated and washed with brine, dried over anhydrous sodium sulfate, and concentrated to a crude residue. The crude material was purified by column chromatography, eluting the desired product from silica gel with a gradient of 10-60% ethyl acetate in hexanes to give 61 mg of the title compound. MS (ESI−): m/z 304.1 (M−1).

Provenance & Evidence