Sodium triacetoxyborohydride → HCID 178489119, compound

Participants

Reaction Steps

To a dry flask was added 4-(5-oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehyde (308 mg, 0.94 mmol) and 2-methoxy-5-(5-piperidin-4-yl-4H-1,2,4-triazol-3-yl)pyridine trifluoroacetate (350 mg, 0.94 mmol) in 5% NEt3:DMF (5 mL). The solution was stirred for 15 min. then 5% AcOH:DMF (10 mL) was added. This was stirred for 1 h and sodium triacetoxyborohydride was added and the reaction mixture was stirred for 16 h at room temperature. The mixture was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate solution and then extracted (×3) with CH2Cl2, the organic layers combined and dried over anhydrous Na2SO4. This was filtered, concentrated and purified by silica gel chromatography (2-4% MeOH in CH2Cl2) to give 2-[4-({4-[5-(6-methoxypyridin-3-yl)-4H-1,2,4-triazol-3-yl]piperidin-1-yl}methyl)phenyl]-3-phenyl-1,6-naphthyridin-5(6H)-one. NMR (MeOD): δ 8.73-8.72 (1H, d, J=3 Hz), 8.52 (1H, s) 8.25-824 (1H, d, J=3 Hz), 7.43-7.41 (1H, d, J=6), 7.33-714 (1H, m), 6.80 (2H, m), 3.93 (3H, s), 3.6 (2H, s), 3.02-2.98 (2H, m), 2.86 (1H, m), 2.27 (2H, m), 2.05 (2H, m), 1.93 (3H, m). m/e (m+1): 570.1.

Provenance & Evidence