Potassium Carbonate → HCID 66890986, compound

Participants

Reaction Conditions

Reaction Steps

To 116.2 mg of tert-butyl 4-methylenepiperidine-1-carboxylate was added a solution of 71.3 mg of 9-borabicyclo[3.3.1] nonane in 2 ml of tetrahydrofuran at room temperature. The reaction mixture was stirred at 90° C. for 1.5 hours, cooled to room temperature, and added to a suspension of 106.8 mg of 2-chloro-6-methyl-N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)pyrimidin-4-amine, 12.3 mg of (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II)-dichloromethane complex, 4.3 mg of triphenylarsine and 49.8 mg of potassium carbonate in 2 ml of N,N-dimethylformamide and 0.2 ml of water. The reaction mixture was stirred at 60° C. for 8 hours. 12.4 mg of (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II)-dichloromethane complex, 4.8 mg of triphenylarsine and 47.3 mg of potassium carbonate was added to the reaction mixture, followed by stirring the reaction mixture at 60° C. for 13 hours, 90° C. for 1.5 hours and 100° C. for 2.5 hours. 13.7 mg of (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II)-dichloromethane complex, 5.0 mg of triphenylarsine, 47.1 mg of potassium carbonate and a solution of tert-butyl 4-(9-borabicyclo[3.3.1]non-9-ylmethyl)piperidine-1-carboxylate (prepared from 117.6 mg of tert-butyl 4-methylenepiperidine-1-carboxylate and 145.2 mg of 9-borabicyclo[3.3.1]nonane in 2.5 ml of tetrahydrofuran at 100° C. for 3 hours) were added to the reaction mixture, followed by stirring the reaction mixture at 100° C. for 4.5 hours. The reaction mixture was cooled to room temperature, poured into water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=8/1 to ethyl acetate) to give the title compound.

Provenance & Evidence