Acetic Acid → 6-(4-{[4-(2-Methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-3-nitro-5-phenylpyridin-2-amine

Participants

Reaction Steps

4-(6-Amino-5-nitro-3-phenylpyridin-2-yl)benzaldehyde (4-2; 0.150 g, 0.470 mmol), 2-methyl-1-piperidin-4-yl-1H-benzimidazole hydrochloride (0.142 g, 0.564 mmol), and NaBH(OAc)3 (0.120 g, 0.564 mmol) were stirred in 2 ml of anhydrous DMF. Triethylamine (0.079 ml, 0.564 mmol) was added followed by addition of acetic acid (0.108 ml, 1.88 mmol). After 2 h the reaction was quenched with saturated aqueous NaHCO3 and extracted 3× with DCM. The combined extracts were dried over Na2SO4, filtered, and concentrated to afford pure 6-(4-{[4-(2-methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-3-nitro-5-phenylpyridin-2-amine (4-3). 1H NMR (CDCl3) δ 8.48 (s, 1H), 7.68 (m, 1H), 7.57 (m, 1H), 7.36 (d, 2H, J=8.1 Hz), 7.27 (m overlapping with CHCl3), 7.20 (m, 2H), 7.16 (m, 2H), 4.15 (m, 1H), 3.58 (s, 2H), 3.05 (d, 2H, J=11.5 Hz), 2.63 (s, 3H), 2.55 (m, 2H), 2.17 (t, 2H, J=11.5 Hz), 1.83 (d, 2H, J=12.0 Hz). MS m/z (M+H)=519.18.

Provenance & Evidence