Sodium hydride → 1-benzenesulfonyl-2-{[cyanomethyl(toluene-4-sulfonyl)amino]methyl}-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester

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Reaction Conditions

Reaction Steps

To a cooled (0° C.) mixture of 1-benzenesulfonyl-2-bromomethyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester (1.64 g, 4.00 mmol) and N-cyanomethyl-4-methyl-benzenesulfonamide (0.93 g, 4.40 mmol) in dry THF (10 mL) was added sodium hydride (0.176 g, 60% dispersion in mineral oil, 4.40 mmol) in two equal portions. The reaction mixture was stirred at 0° C. for 15 minutes then allowed to warm to room temperature. After 66 h the reaction mixture was diluted with DCM (60 mL) and saturated aqueous sodium carbonate solution (25 mL). The layers were separated and the aqueous phase was extracted with DCM (2×25 mL). The combined organic phase was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was triturated with THF (5 mL) and the resultant solid dried in vacuo to afford the title compound as a beige solid (1.72 g, 80%). LCMS (Method B): RT=3.91 min, M+H+=539.

Provenance & Evidence