Ammonium Chloride → {1-[4-(7-Acetyl-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

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Reaction Conditions

Reaction Steps

To a solution of (1-{4-[7-(methoxy-methyl-carbamoyl)-3-phenyl-imidazo[1,2-a]pyridin-2-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester [prepared in a manner analogous to that described in Int-24-0] (250 mg, 0.48 mmol) in THF (10 mL) under an atmosphere of argon at 0° C. was added a 3 M solution of methyl-magnesium chloride in THF (0.4 mL, 1.2 mmol, 2.5 equiv). The resulting was stirred for 1 h at 0° C., then for 5 h at room temperature. The resulting material was added to a saturated aqueous NH4Cl solution (10 mL). The resulting mixture was extracted with EtOAc (3×20 mL). The combined organic phases were dried (Na2SO4 anh) and concentrated under reduced pressure. The remaining material was purified using MPLC (Biotage Isolera; 25 g SNAP cartridge: 100% hexane for 1 min., gradient to 75% hexane/25% EtOAc over 1 min., 75% hexane/25% EtOAc for 3 min., gradient to 50% hexane/50% EtOAc over 1 min., 50% hexane/50% EtOAc for 4.5 min, gradient to 25% hexane/75% EtOAc over 2.5 min., gradient to 100% EtOAc over 2 min., 100% EtOAc for 10.6 min.) to give {1-[4-(7-acetyl-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (151 mg, 66%):

Provenance & Evidence