Methanol → HCID 10207712, compound

Participants

Reaction Steps

A solution of 690 mg (1.19 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide, 0.33 ml (2.4 mmol) triethylamine and 1.9 ml (48 mmol) methanol in 10 ml N,N-dimethylformamide was deoxygenated by three freeze-thaw cycles. Filling the flask with carbon monoxide gas from a balloon was followed by addition of 31 mg (0.12 mmol) triphenylphosphine and 23 mg (0.102 mmol) palladium(II) acetate. The reaction mixture was stirred for 60 h under an atmosphere of carbon monoxide gas at room temperature. The mixture was diluted with water and extracted with 3 portions of tert-butyl methyl ether. The combined organic extracts were washed with water, dried with sodium sulfate and concentrated. Flash chromatography afforded 407 mg (66.8%) of the title compound as a light-yellow solid.

Provenance & Evidence