2-(Tributylstannyl)-1,3-thiazole → HCID 136389262, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (246 mg, 0.65 mmole), 2-(tributylstannyl)thiazole (410 μl, 1.30 mmole) and bis(triphenylphosphine)-palladium(II) dichloride (46 mg, 0.06 mmole) in dimethylformamide (3 ml) was stirred at 130° C. for one hour before it was cooled to room temperature, quenched with water, filtered. The filtrate was partitioned between ethyl acetate 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 ethyl acetate and hexanes. Fractions containing the title compound was concentrated and repurified by preparative TLC with a gradient of methanol, dichloromethane and acetic acid to give the title compound as a yellow solid (29 mg). MS: (+) m/z 383.87 (M+1), m/z 406.00 (M+Na+).

Provenance & Evidence