HCID 53973988, compound → HCID 22615028, compound

Participants

Reaction Steps

To a solution of [3-(2-ethoxymethyl-3-methyl-benzofuran-4-yloxy)-propyl]-pyridin-3-ylmethyl-carbamic acid benzyl ester (19 mg) in ethyl acetate (1 ml) was added 5% Pd on charcoal catalyst (10 mg) under N2. The nitrogen atmosphere was replaced by hydrogen (1 atom) and the resulting mixture was stirred overnight at room temperature. The reaction mixture was filtered through a pad of celite and washed with methanol and dichloromethane. The filtrate combined was concentrated in vacuo. The residue was purified by preparative thin layer chromatography (using dichloromethane : MeOH : ammonia solution (25-28%)=10:1:0.2 as a developing solvent) to give [3-(2-ethoxymethyl-3-methyl-benzofuran-4-yloxy)-propyl]-pyridin-3-ylmethyl-amine (9 mg) as a colorless oil. ESI-MS: m/z 355 (MH+); 1H-NMR (CDCl3): δ 1.24 (3H, t, J=7 Hz), 2.06 (2H, quintet, J=6.5 Hz), 2.31 (3H, s), 2.89 (2H, t, J=7 Hz), 3.56 (2H, q, J=7 Hz), 3.85 (2H, s), 4.14 (2H, t, J=6 Hz), 4.54 (2H, s), 6.58 (1H, d, J=8 Hz), 7.04 (1H, d, J=8 Hz), 7.14 (1H, t, J=8 Hz), 7.21 (1H, dd, J1=8 Hz, J2=5 Hz), 7.68 (1H, dd, J1=8 Hz, J2=2 Hz), 8.49 (1H, dd, J1=5 Hz, J2=2 Hz), 8.57 (1H, d, J=2 Hz).

Provenance & Evidence