Indole-3-Carboxaldehyde → HCID 131732019, compound

Participants

Reaction Steps

Indole-3-carbaldehyde (1 eq.) was dissolved in DMF (0.15 M). Sodium hydride was added (1.3 eq.) and the resulting solution was stirred at RT for 20 min. Tetrabutylammonium iodide (1 eq.) and tert-butyl 3-bromopropylcarbamate (2 eq.) were then added and the reaction solution was allowed to stir at RT for 18 h. The reaction mixture was subsequently quenched with sat. aq. NH4Cl and extracted with EtOAc. The combined organic extracts were dried over MgSO4. Filtration and concentration of the filtrate in vacuo afforded a yellow oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 7:3 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a light pink solid.

Provenance & Evidence