Oxalyl chloride → HCID 22603434, compound

Participants

Reaction Steps

To a stirred solution of ethyl N-(3,4-dichlorobenzyl)-2-ethoxycarbonylindole-3-carboxylic acid (100 mg) in dichloromethane (4 ml) at ambient temperature, under argon, was added DMF (1 drop) and oxalyl chloride in dichloromethane (2M, 153 μl). The reaction was stirred at ambient temperature for 7 hours, then concentrated in vacuo and dissolved in dichloromethane (4 ml). Tetrahydrofurfurylamine (53 μl) was added, followed by triethylamine (71 μl) and the reaction stirred under argon for 16 hours. The reaction was diluted with dichloromethane (30 ml), washed with HCl (2M, 30 ml) and water (30 ml), dried (MgSO4) and concentrated in vacuo to give a crude residue which was purified by column chromatography, using ethyl acetate:iso-hexane as eluent (gradient 10/90-50/50), to give the product as an off-white solid (57 mg, 47%); M/z (+) 475.3 (MH+),

Provenance & Evidence