Triethylamine → 4-[2-(2,6-Difluorophenyl)-4,5-dihydro-4-oxazolyl]-N-(4-fluorophenyl)benzamide

Participants

Reaction Conditions

Reaction Steps

The compound of Example 2 (1.0 g, 3 mmol) and 4-fluoroaniline (0.33 g, 3 mmol) were dissolved in dimethylsulfoxide (20 mL) and treated with triethylamine (1 mL) and bis (diphenylphosphino) propane (0.1 g, 2 mmol). Carbon monoxide was bubbled through the mixture for 5 min and palladium acetate (0.05 g, 2 mmol) was added. The mixture was evacuated with carbon monoxide was released into the reaction by means of a balloon. The evacuation and carbon monoxide release was repeated and the reaction was heated to 70° C. under a carbon monoxide atmosphere for 6 h. The compound, 4-fluoroaniline (0.33 g. 3 mmol), was added and heating continued for 1 h. The mixture was allowed to stand overnight and was added to water (100 mL). The solid form was filtered, taken up in a mixture of dichloromethane and ethyl acetate, and dried over magnesium sulfate. The residue, after evaporation under reduced pressure, was subjected to chromatography on silica gel with hexanes/ethyl acetate (3:1 to 1:2) as eluent. The title compound (0.45 g) was a slightly orange solid: m.p. 210°-212° C. 1H NMR (DMSO-D6, 200 MHz) δ 10.4 (b s,NH), 8.0-7.2 (m,11H), 5.6 (m,1H), 4.8 (m,1H), 4.3 (m,1H).

Provenance & Evidence