Tetramethyltin → 7-Hydroxy-4-methyl-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester

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Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a mixture of 4-bromo-7-hydroxy-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester (200 mg, 0.573 mmol), tetramethyltin (0.32 mL, 2.29 mmol), and dichlorobis(triphenylphosphine)palladium(II) (40.2 mg, 0.057 mmol) was suspended in 4.8 mL of anhydrous N,N-dimethylformamide. The reaction mixture was heated at 130° C. for 1 hour, cooled to room temperature, and diluted with ethyl acetate. The organic mixture was successively washed with saturated sodium bicarbonate solution, brine, saturated ammonium chloride solution, and brine. The organic phase was dried over anhydrous sodium sulfate and concentrated. The residue was purified by flash chromatography eluting from silica gel with a gradient of 0-100% ethyl acetate in hexanes to give 99.6 mg of the title compound as a white solid. MS: (+) m/z 285.0 (M+1).

Provenance & Evidence