2-Methoxyethylamine → HCID 59205420, compound

Participants

Reaction Steps

5-Cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carboxylic acid (1.00 g, 2.77 mmol) was suspended in anhydrous DCM (20 ml) and thionyl chloride (0.5 ml, 6.85 mmol) added. The reaction was heated under reflux for 3 h then evaporated to dryness. The residue was dissolved in anhydrous DCM and spit into 4 aliquots, one aliquot was added to a solution of methoxyethylamine (0.075 ml, 1.00 mmol) and triethylamine (0.14 ml, 1.00 mmol) in DCM (5 ml). After stirring for 2 h the reaction was washed with water (2 ml) then evaporated to dryness. Crude product was purified by silica chromatography using DCM as eluent then crystallised from DCM:diethyl ether to provide crystalline title compound.

Provenance & Evidence