Methanol → HCID 58497930, compound

Participants

Reaction Steps

To a solution of 7-bromo-4-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl)-2-methyl-benzo[d]oxazole (3.5 g) in dimethylformamide (40 ml) was added successively triethylamine (2.5 ml), methanol (60 ml) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (“PdC12(dppf)”) (259 mg). The reaction mixture was stirred in a pressure reactor in an atmosphere of carbon monoxide (4 bar) at 80° C. for 16 hours. The reaction mixture was cooled to ambient temperature, filtered over a plug of Celite® and concentrated. The residue was purified by column chromatography on silica gel (eluent: 15-55% v/v ethyl acetate in heptane) to give 4-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl)-2-methyl-benzo[d]oxazole-7-carboxylic acid methyl ester (2.75 g). 1H-NMR (400 MHz, CDCl3): 7.95-7.42 (m, 5H), 4.56 (d, 1H), 4.12 (d, 1H), 4.02 (s, 3H), 2.77 (s, 3H) ppm.

Provenance & Evidence