Potassium Phosphate, Tribasic → HCID 58129453, compound

Participants

Reaction Conditions

Reaction Steps

Combine [1-(6-bromo-pyridin-2-yl)-1-methyl-ethyl]-carbamic acid tert-butyl ester (1.64 g, 7.6 mmol), cyclopropyl boronic acid (850 mg, 9.9 mmol), potassium phosphate (6.1 g, 26.6 mmol), and palladium acetate (85 mg, 0.38 mmol). Add toluene (31 mL) and water (1.4 mL) followed by 1M tricyclohexyl phosphine in toluene (760 μl, 0.76 mmol); degas the mixture, purge with nitrogen, and heat at 100° C. for 6 hours, then stir at room temperature overnight. Add tri tert-butylphosphine (153 mg, 0.76 mmol) and palladium acetate (85 mg, 0.38 mmol), degas and heat at 85° C. overnight. Filter the reaction and purify the filtrate over silica (120 g) eluting with 0% to 25% EtOAc:hexanes to give [1-(6-cyclopropyl-pyridin-2-yl)-1-methyl-ethyl]-carbamic acid tert-butyl ester as an oily yellow solid (1.3 g, 62%). MS (m/z): 277.4 (M+H)+.

Provenance & Evidence