3-Hydroxybenzaldehyde → 3-{[(3-Chloro-4-fluorophenyl)(2-hydroxy-1-methylethyl)amino]methyl}phenol

Participants

Reaction Conditions

Reaction Steps

2-[(3-chloro-4-fluorophenyl)amino]propan-1-ol (1-4, 0.030 g, 0.147 mmol) in DCE (1.0 mL) was treated with NaCNBH3 (0.019 g, 0.295 mmol), and 3-hydroxylbenzaldehyde (0.036 g, 0.295 mmol). The resulting mixture stirred at 25° C. for 24 h then concentrated. The reaction was purified by reverse phase liquid chromotography (Semi-prep YMC C-18 Column 5% CH3CN/H2O up to 95% CH3CN/H2O) to give 3-{[(3-chloro-4-fluorophenyl)(2-hydroxy-1-methylethyl)amino]methyl}phenol (1-5). 1H NMR (300 MHz, CDCl3) δ 7.15 (m, 3H), 6.89 (m, 2H), 6.71 (m, 2H), 4.44 (d, J=10.0 Hz, 2H), 4.00 (m, 1H), 3.73 (s, 2H), 1.19 (d, J=6.7 Hz, 3H). MS 310.3 found, 310.7 (M+H+) required.

Provenance & Evidence