Dimethylformamide → HCID 118093605, compound

Participants

Reaction Conditions

Reaction Steps

Bubble nitrogen gas through a solution of 1-[4-(6-chloro-2-methyl-pyrimidin-4-yl)oxyphenyl]-N-methyl-methanesulfonamide (26.6, 81.1 mmol) in DMF (266.0 mL) for 15 minutes. Thereafter add zinc cyanide (14.59 g, 121.2 mmol) and (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) chloride (6.76 g, 8.1 mmol). Heat the suspension to 150° C. for 6 hr while maintaining it under a nitrogen atmosphere. Cool the mixture to room temperature. Dilute the mixture with water (600 mL) and extract the mixture with EtOAc (3×500 mL). Combine the EtOAc extracts. Sequentially wash the combined extracts with water (500 mL) then brine (500 mL); dry over sodium sulfate; filter and concentrate the filtrate under reduced pressure. Isolate the title compound using silica gel chromatography eluting with hexane/EtOAc (1:1) to give the title compound (18 g, 70%). MS (m/z): 319 (M+1).

Provenance & Evidence