4-tert-Butylbenzaldehyde → HCID 86603114, compound

Participants

Reaction Steps

81 mg (0.5 mmol) of 4-tert-butyl benzaldehyde and 92 mg (0.5 mmol) of N-(4-chloro-phenyl)-N-methyl-ethane-1,2-diamine were dissolved in 2 ml methanol and the solution was stirred for 2 h at rt. 18.5 mg (0.5 mmol) of sodium borohydride were added in portions under nitrogen. The reaction mixture was stirred at rt for 30 min, the solvent was evaporated and the residue was suspended in 4 ml DCM. 88 mg (0.55 mol) of 1H-indole-7-carboxylic acid and 105 mg (0.55 mmol) of EDC.HCl were added and the mixture was stirred at rt over night. The product was purified by column chromatography (silica gel, diethyl ether) to yield 140 mg (59%) product as a colorless oil. MS (ISP) 474.4 (M+H)+.

Provenance & Evidence