Sodium hydride → 4-Bromo-1,6-dihydro-6-methyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-c]pyridin-7-one

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Reaction Conditions

Reaction Steps

A solution of 4-bromo-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one (0.967 g, 4.26 mmol) in N,N-dimethylformamide (30.6 mL) at 0° C. was treated with sodium hydride (0.255 g, 6.38 mmol) and stirred at 0° C. for 30 min. After this time the reaction mixture was treated with [β-(trimethylsilyl)ethoxy]methyl chloride (1.13 mL, 6.39 mmol) and subsequently stirred at 20° C. for 1 h. The reaction mixture was diluted with ethyl acetate and water. Layers were separated and the organic layer was washed with water (3×), dried with magnesium sulfate, filtered, and concentrated to give a crude residue. Purification by flash column chromatography (100% hexanes to 30% EtOAc/hexanes) gave the desired product (1.03 g, 68%) as a white solid. LCMS calculated for C14H22BrN2O2Si (M+H)+: m/z=357.1, 359.1. found: 357.0, 359.0.

Provenance & Evidence