Triethylamine → HCID 11733337, compound

Participants

Reaction Steps

A stirred solution of 2.43 g (10 mmol) of (S)-8-(acetoxymethyl)-6,7,8,9-tetrahydropyrido [1,2-a]indole (prepared as described in Example 2) in 15 ml of dichloromethane was treated at 0° C. with a solution of 1.27 g (10 mmol) of oxalyl chloride in 5 ml of dichloromethane. The solution was stirred for 15 minutes and then treated with 2.67 g (10 mmol) of isopropyl 1-methyl-3-indoleacetimidate hydrochloride (prepared as described in Example 1) followed by 10 ml of dichloromethane. The mixture obtained was treated with 5.05 g (10 mmol) of triethylamine, allowed to warm to room temperature and stirred for 2 hours. The mixture was then washed with water and the organic layer was dried over magnesium sulfite and evaporated to dryness. The residue was dissolved in 30 ml of pyridine, cooled in ice and treated dropwise with 2.10 g (10 mmol) of trifluoroacetic anhydride over 2-3 minutes. After 15 minutes, the solvent was evaporated in vacuo and the residue was partitioned between dichloromethane and 2M hydrochloric acid. The organic layer was washed with water and saturated sodium bicarbonate solution, dried over magnesium sulfite and evaporated. The residue was triturated with 30 ml of methanol and the solid was removed by filtration. The product was washed with methanol and dried to give 2.45 g (52%) of (S)-3-[8-(acetoxymethyl)-6,7,8,9-tetrahydro-pyrido [1,2-a]indol- 10-yl]-4(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione in the form of a red solid of melting point 238°-241° C.

Provenance & Evidence