Methyl Acrylate → (E)-3-{2-[4-(1-tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridin-7-yl}-acrylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a mixture of {1-[4-(7-bromo-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (534 mg, 1.03 mmol), methyl acrylate (0.19 mL, 2.06 mmol, 2.0 equiv), triethylamine (0.16 mL, 1.17 mmol, 1.1 equiv), palladium(II) acetate (17 mg, 0.08 mmol, 7 mol %) and tri (2-tolyl)phosphine (53 mg, 0.18 mmol, 17 mol %) in acetonitrile (7 mL) was heated at 150° C. for 2 h. in a microwave apparatus. The reaction mixture was mixed with water (10 mL), a saturated aqueous NH4Cl solution (10 mL) and CH2Cl2 (25 mL) with vigorous stirring at room temperature for 30 min. The resulting organic phase was washed with a saturated aqueous NaCl solution, dried (Na2SO4 anh), and concentrated under reduced pressure to give (E)-3-{2-[4-(1-tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridin-7-yl}-acrylic acid methyl ester (452 mg, 75%):

Provenance & Evidence