1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 46179269, compound

Participants

Reaction Conditions

Reaction Steps

200 mg (0.352 mmol) of 6-bromo-1-{3-[5-(2-morpholin-4-ylethoxy)pyrimidin-2-yl]benzyl}-1H-benzotriazole, 80.6 mg (0.387 mmol) of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 150 mg (0.704 mmol) of tripotassium phosphate trihydrate are suspended in 6 ml of ethylene glycol dimethyl ether, degassed evacuated and flushed with nitrogen a number of times. 24.7 mg (0.035 mmol) of bis(triphenylphosphine)palladium(II) chloride are added, and the mixture is again evacuated and flushed with nitrogen. The reaction mixture is stirred at 80° C. for 24 h. Water is added to the reaction mixture, which is then rendered basic using 32% NaOH and extracted with DCM. The organic phase is dried over sodium sulfate, evaporated under reduced pressure in a rotary evaporator and purified by column chromatography on silica gel; yield: 41 mg, HPLC: Rt=2.08 min (method C), LC-MS: [M+H]+=497;

Provenance & Evidence