Triethylamine → HCID 86587685, compound

Participants

Reaction Steps

A solution of 2-(3-cyano-1H-indol-5-ylmethyl)-cyclopropanecarboxylic acid (0.080 g, 0.33 mmol), N, N-dimethylhydroxylamine hydrochloride (0.065 g, 0.67 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.077 g, 0.40 mmol), triethylamine (0.13 g, 1.33 mmol), and dichloromethane (5 ml) was stirred at ambient temperature for 1 h then diluted further with an additional 10 ml dichloromethane. The solution was washed with 1N hydrochloric acid (1×5 ml), 1N sodium hydroxide (1×5 ml), and brine (1×5 ml) and dried over anhydrous sodium sulfate. The filtrate was concentrated in vacuo to afford 2-(3-cyano-1H-indol-5-ylmethyl)-cyclopropanecarboxylic acid methoxy-methyl-amide (0.075 g, 79%) as a light brown film. 1H-NMR (400 MHz, CDCl3) 7.69 (1H, m), 7.57 (1H, s), 7.22 (1H, d, J=2.7 Hz), 7.11 (1H, d, J=1.52 Hz), 3.69 (3H, s), 3.20 (3H, s), 2.81 (2H, m), 2.10 (1H, m), 1.73 (1H, m), 1.28 (1H, m), 0.91 (1H, m).

Provenance & Evidence