4-tert-Butylbenzaldehyde → HCID 86603115, compound

Participants

Reaction Steps

81 mg (0.5 mmol) of 4-tert-butyl benzaldehyde and 68 mg (0.5 mmol) of N-phenyl ethylene 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 80 mg (37%) product as a colorless oil. MS (ISP) 426.5 (M+H)+.

Provenance & Evidence