N,N-Dimethylglycine → HCID 67003419, compound

Participants

Reaction Steps

A solution of 5-bromoindoline (0.5 g, 2.52 mmol), 1-hydroxybenzotriazole hydrate (0.387 g, 2.52 mmol), N-methylmorpholine (1.11 mL, 10.1 mmol) and 2-(dimethylamino)acetic acid (0.299 g, 2.9 mmol) in N,N-dimethylformamide (9.5 mL) was treated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.678 g, 3.53 mmol) and the reaction was stirred at ambient temperature for 18 hours. The reaction was diluted with water (100 mL) and extracted with 1:1 ether/ethyl acetate (2×120 mL). The combined organic layers were washed with water (2×80 mL) and brine (2×80 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by flash chromatography on a silica gel column eluting with a gradient of from 0% to 5% methanol in dichloromethane to provide the title compound. MS DCI (+) m/z 283.0 [M+H]+.

Provenance & Evidence