Potassium Phosphate, Tribasic → Tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidine-1-carboxylate (703 mol), quinolin-3-ylboronic acid (350 mg, 2.00 mmol), Pd(dppf)Cl2—CH2Cl2 (82 mg, 0.10 mmol) and potassium phosphate (636 mg, 3.0 mmol) in a mixture of dioxane/H2O (9:1, 20 mL) was heated at 100° C. for 5 h under argon. The reaction mixture was cooled down and diluted with EtOAC, washed with Brine, dried over Na2SO4, filtered and concentrated. The residue was purified by Biotage (CH2Cl2/EtOAc, 10:1 to 3:1) to give the title compound as brown solid. LC/MS RT=2.49 min. Mass calculated for, M+H 690.37, observed 389.17.

Provenance & Evidence