2,4-Dimethoxybenzaldehyde → HCID 18320739, compound

Participants

Reaction Steps

A solution of 2.0 g (5.69 mmol) of [1-carbamoyl-2-(3-indolyl)-2-oxoethyl]-carbamic acid benzyl ester in 160 ml ethyl acetate:acetic acid:ethanol (1:2:1) was hydrogenolyzed at atmospheric pressure over 0.45 g of 10% Pd(C) for 3 h. The mixture was filtered and concentrated. 2.41 g (11.4 mmol) of NaBH(OAc)4 was added in portions to a solution of the residue and 0.95 g (5.69 mmol) of 2,4-dimethoxybenzaldehyde in 30 ml of DMF:HOAc (1:1). After 18 h at room temperature the reaction mixture was concentrated and purified by chromatography on SiO2 (PhMe—CH2Cl2—MeOH—NEt3, 30:60:20:2). The solid product was washed with ether to give the title compound (1.78 g, 85%).

Provenance & Evidence