Trifluoroacetic acid → HCID 118021326, compound

Participants

Reaction Steps

Add TFA (114.4 mmol) to a solution of 4-bromobenzaldehyde (76.2 mmol), 4-methylindole (76.2 mmol), and triethylsilane (228.4 mmol) in dichloromethane (10 mL) pre-cooled in an ice bath. Allow the mixture to warm to room temperature and stir for 2 hours. Add additional triethylsilane (228.4 mmol) and warm the mixture to 30° C. overnight in an oil bath. Dilute the reaction with water (100 mL) and extract with dichloromethane (2×100 mL). Separate and wash the organic phase with water (2×100 mL) and brine (100 mL). Dry the organic phase over sodium sulfate, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography over silica gel (120 g cartridge) eluting with 0-10% ethyl acetate in petroleum ether to yield the title compound (8 g, 26.6 mmol): MS (m/z): 301 (M+1)

Provenance & Evidence