Stannane, tributyl(1-ethoxyethenyl)- → Tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(1-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate

Participants

Reaction Conditions

Reaction Steps

A degassed mixture of tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (256 mg, 0.31 mmol), Pd(PPh3)4 (35 mg, 0.031 mmol), tributyl(1-ethoxyvinyl)stannane (221 mg, 0.61 mmol) in dioxane (6 mL) was heated at 100° C. overnight. The reaction mixture was cooled to room temperature, filtered through a 9:1 SiO2:KF plug and concentrated in vacuo. Purification by column chromatography afforded tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(1-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate, LCMS tR=3.58 Min (10 min run, UV254nm). Mass calculated for M+H 828.45, observed LC/MS m/z 828.07 (M+H).

Provenance & Evidence