Triethylamine → N-methyl-N-(1-methyl-1H-pyrrolo[2,3-b]pyridin-ylmethyl)acrylamide

Participants

Reaction Steps

A solution of acryloyl chloride (0.43 g, 5.58 mmole) in CH2Cl2 (10 mL) was added dropwise with stirring to a solution of 1-methyl-3-(methylaminomethyl)-1H-pyrrolo[2,3-b]pyridine (0.93 g, 5.28 mmole) and triethylamine (0.8 mL, 5.8 mmole) in CH2Cl2 (40 mL) at 0° C. under N2. The reaction was allowed to warm to RT and stir for 1 hr, then was concentrated in vacuo. The residue was dissolved in 10% NaOH and extracted with CH2Cl2 (3×20 mL). The extracts were dried (MgSO4), filtered, and concentrated. The residual oil was flash chromatographed on silica gel (5% MeOH/CH2Cl2) to give the title compound (1.0 g, 80%) as a colorless oil: MS (ES) m/e 216 (M+H)+.

Provenance & Evidence