Acetic Acid → HCID 21103104, compound

Participants

Reaction Steps

To a solution of 4-(3-phenyl-1,8-naphthyridin-2-yl)benzaldehyde (9-3) (135 mg, 0.44 mmole) in dry DMF (2 mL) was added 1-piperidin-4-yl-1,3-dihydro-2H-benzimidazol-2-one (123 mg, 0.57 mmole) and HOAc (0.13 mL, 2.18 mmole) at RT. After 30 min NaBH(OAc)3 (120 mg, 0.57 mmole) was added. After 4 hr the mixture was concentrated. The residue was taken up in saturated NaHCO3 and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated. Flash column (gradient, 0–10% MeOH/CH2Cl2) gave the title compound as a cream colored solid (9-4): 1H-NMR (500 MHz, CDCl3) δ 9.15 (dd, J=1.71, 2.44 Hz, 1 H), 8.56 (bs, 1 H), 8.24 (m, 1 H), 8.19 (s, 1 H), 7.53 (m, 2 H), 7.30 (m, 7 H), 7.06 (m, 3H), 4.36 (m, 1 H), 3.56 (s, 2 H), 3.01 (d, J=11.47 Hz, 2 H), 2.44 (m, 2 H), 2.17 (m, 2H), 1.79 (d, J=11.72 Hz, 2 H); HRMS, calc'd for C33H29N5O (M+1), 512.2445; found 512.2478.

Provenance & Evidence