Methanol → HCID 66790291, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-4-(4-fluorophenyl)-2,2-dimethyl-7-nitro-2H-1,4-benzoxazin-3(4H)-one (compound obtained in Reference Example 50(2); 400 mg), palladium acetate (5.1 mg), racemic 2-(di-tert-butylphosphino)-1,1′-binaphthyl (11.4 mg), cesium carbonate (557 mg), methanol (1 mL) and toluene (4 mL) was stirred at 70° C. under argon atmosphere for 26 hours. After cooling, to the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The resultant residue was suspended in chloroform (4 mL) and thereto was added 1-hydroxybenzotriazole (154 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (208 mg). The mixture was stirred at room temperature for 3 hours. To the reaction mixture was added water, and the mixture was extracted with chloroform. The organic layer was washed successively with an aqueous saturated sodium hydrogencarbonate solution and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on NH-silica gel (Chromatorex NH-silica gel; solvent; n-hexane/ethyl acetate=9/1) to give 4-(4-fluorophenyl)-6-methoxy-2,2-dimethyl-7-nitro-2H-1,4-benzoxazin-3(4H)-one (147 mg) as a pale yellow powder.

Provenance & Evidence