Potassium Phosphate, Tribasic → {1-[4-(7-Cyclopropyl-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

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Reaction Conditions

Reaction Steps

A mixture of {1-[4-(7-bromo-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (200 mg, 0.38 mmol), cyclopropylboronic acid (166 mg, 1.93 mmol, 5.0 equiv), tetrakis(triphenylphosphine)palladium(0) (18 mg, 0.015 mmol, 4 mol %) and K3PO4 (164 mg, 0.77 mmol, 2.0 equiv), in toluene (4.5 mL) was heated at the reflux temperature for 16 h with monitoring by UPLC-MS. The resulting mixture was heated at 90° C. for 1 h in a microwave apparatus, then concentrated under reduced pressure. The remaining material was treated with water (25 mL), and was then extracted with EtOAc (2×25 mL). The combined organic phases were washed with water (25 mL), dried (Na2SO4 anh), and concentrated under reduced pressure. The remaining material (205 mg) was was purified using MPLC (Biotage Isolera Flash NH2 Snap 10 reverse phase column; 100% CH2Cl2 for 1 min., gradient to 90% CH2Cl2/10% MeOH over 10 min.; 90% CH2Cl2/10% MeOH for 4 min.) to give {1-[4-(7-cyclopropyl-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (162 mg, 87%):

Provenance & Evidence