Ethanol → 5-{5-[(Benzyl-ethyl-amino)-methyl]-pyridin-3-yl}-3-methyl-3H-benzooxazol-2-one

Participants

Reaction Steps

A mixture of 5-(5-(Benzylamino-methyl)-pyridin-3-yl)-3-methyl-3H-benzooxazol-2-one (crude from step 2, ˜0.39 mmol) and Pd(OH)2 (20 mg, 10%) in ethanol (10 mL) and acetic acid (0.5 mL) was stirred under 1 atmosphere of H2 at room temperature for 48 h. After filteration and concentration, the residue was purified by flash column (MeOH—CH2Cl2, v/v, 0-5%) and yielded yellow solid (3 mg), ESI-MS m/z: 387.9 [M+1]+, Retention time 1.45 min; 1HNMR (CDCl3, 400.342 MHz) δ 1.48 (t, J=7.2 Hz, 3H), 3.05 (s, 2H), 3.48 (s, 3H), 4.23 (s, 2H), 4.05-4.27 (m, 2H), 7.21 (s, 1H), 7.23 (5, 1H), 7.40-7.43 (m, 3H), 7.62-7.64 (m, 2H), 7.83 (s, 1H), 8.52 (5, 1H), 8.85 (d. J=1.84 Hz, 1H), 9.21 (s, 1H).

Provenance & Evidence