Sodium hydride → 5-bromo-2-[(tert-butoxycarbonyl-ethoxycarbonylmethyl-amino)-methyl]-1-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

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Reaction Conditions

Reaction Steps

5-bromo-2-bromomethyl-1-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester (400 mg, 0.94 mmol) and tert-butoxycarbonylamino-acetic acid ethyl ester (182 mg, 0.897 mmol) were dissolved in dry N,N-dimethylformamide (7 mL) at 0° C. Sodium hydride (44 mg, 1.08 mmol) was then added in one portion; the mixture was stirred for 30 min at 0° C., quenched by addition of saturated ammonium chloride aqueous solution, and then extracted with ethyl acetate. The organic phase was subsequently washed with saturated sodium chloride aqueous solution, dried with anhydrous sodium sulfate, and filtered, concentrated to give an oil, which was purified by column to give the title compound (392 mg); ESI MS (m/z): 531 (M+Na+).

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