Water → HCID 67457655, compound

Participants

Reaction Steps

A flask charged with 7-(4-bromophenyl)-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (Preparation L; 0.200 g, 0.425 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.195 g, 0.935 mmol), potassium phosphate (0.271 g, 1.28 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.0507 g, 0.106 mmol), and tris(dibenzylideneacetone)dipalladium (0.0389 g, 0.0425 mmol) was evacuated and backfilled with argon. To the reaction was added 4 mL of isopropanol (degassed with argon for 30 minutes) and water (0.0460 mL, 2.55 mmol). The reaction was sealed and allowed to proceed at 100° C. for 4 hours. The reaction was then diluted with DCM (100 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting crude was then purified by means of silica gel chromatography eluting with a linear gradient of 1-5% methanol in DCM to afford 7-(4-(1-methyl-1H-pyrazol-4-yl)phenyl)-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (0.174 g, 0.365 mmol, 85.9% yield). MS (apci) m/z=472.2 (M+H).

Provenance & Evidence