1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59318122, compound

Participants

Reaction Steps

A slurry of 1-ethyl-6-nitro-1H-indole (100 mg, 0.52 mmol) and 10% Pd/C (21 mg) in EtOH was hydrogenated under 1 atm of H2 for 2 h. The mixture was filtered and concentrated and the intermediate amine was dissolved in CH2Cl2 (5 mL) and treated with 1-(4-carboxy-phenyl)-piperidine-4-carboxylic acid ethyl ester (110 mg, 0.39 mmol) and EDCI (228 mg, 1.19 mmol). After stirring overnight the reaction mixture was partitioned between EtOAc and water. The EtOAc layer was collected, filtered and concentrated. The residue was chromatographed with 20-60% EtOAc in hexanes to afford the product (57 mg, Yield: 34%). HRMS m/z calcd for C25H29N3O3 [M+H]+: 420.2282. Found: 420.2280.

Provenance & Evidence