Dichloromethane → tert-butyl 2-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-5-methoxy-1H-indole-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-ylboronic acid (0.24 mmol, 70 mg), K3PO4 (0.36 mmol, 77 mg), and PdCl2(dppf).CH2Cl2 (0.012 mmol, 9.8 mg) were added to a solution of 5-chloro-3-(6-phenylpyridin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (0.12 mmol, 72 mg) in dioxane (4 mL) and H2O (0.5 mL). The resulting solution was stirred at 90° C. under argon overnight. The mixture was diluted with H2O and then extracted with ethyl acetate (×2). The combined organic layers were washed with brine and dried with Na2SO4. Evaporation and purification by column chromatography afforded tert-butyl 2-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-5-methoxy-1H-indole-1-carboxylate, LCMS tR=3.48 Min (5 min run, UV254nm). Mass calculated for, M+ 792.3, observed LC/MS m/z 793.2 (M+H).

Provenance & Evidence