3-(2-Bromoethyl)indole → HCID 66932497, compound

Participants

Reaction Steps

TEA (0.46 ml, 3.3 mmol) and 3-(2-bromoethyl)-1H-indole (193 mg, 0.863 mmol) were added to a suspension of (E)-3-{4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester hydrochloride (220 mg, 0.66 mmol, Intermediate 1) in DCM (5 ml), and the mixture was stirred at RT overnight. DCM was evaporated and the residue was dissolved in DMF and heated at 60° C. overnight. The mixture was partitioned between water and AcOEt and the aqueous phase was extracted with DCM. The collected organic phases were dried over Na2SO4 and evaporated. The crude mixture was purified by column chromatography (eluent: DCM/MeOH/NH4OH 94:6:0.2) to give (E)-3-{1′-[2-(1H-indol-3-yl)ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (130 mg).

Provenance & Evidence