Triethylamine → HCID 44211255, compound

Participants

Reaction Steps

A mixture of acid (D4, 1.22 g, 9.8 mmol), 5-amino-1-methyl indole (D2, 1.43 g, 9.8 mmol), triethylamine (1.4 ml) and diphenylphosphoryl azide (2.1 ml, 10 mmol) in 1,4-dioxan (100 ml) was heated under reflux overnight. The mixture was evaporated and the residue was dissolved in dichloromethane and washed with 5% citric acid, sat. sodium bicarbonate and water. The organic phase was dried and evaporated and the residue was chromatographed on silica (100 g) eluted with 2-15% methanol/dichloromethane. Combination of appropriate fractions followed by recrystallisation from dichloromethane/methanol gave pure (E3, 0.70 g). mp 210°-213° C.

Provenance & Evidence