Sodium borohydride → HCID 67305210, compound

Participants

Reaction Steps

A 100 mL round bottom flask equipped with a magnetic stirbar was charged with Intermediate 4B, 1,5-naphthyridine-2-carbaldehyde (200 mg, 1.265 mmol). Ethanol (12.6 mL) was added to give a solution. To this stirred solution was added, portionwise, sodium borohydride (47.8 mg, 1.265 mmol). The reaction mixture was stirred at ambient temperature for 15 minutes, then quenched with aqueous sodium bicarbonate. Volatiles were removed under reduced pressure and the residue was partitioned between EtOAc and water. The aqueous layer was extracted once more with EtOAc, then the combined organic layers were dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to give (1,5-naphthyridin-2-yl)methanol as a pale yellow solid that was purified by eluting through a plug of silica gel with 100% EtOAc. After evaporation of the solvent under reduced pressure, an off white solid was obtained, which was dried in a vacuum oven at ambient temperature for 3 days to give (1,5-naphthyridin-2-yl)methanol (142 mg, 70%). 1H NMR (300 MHz, methanol-d4) δ 8.94 (dd, J=4.3, 1.6 Hz, 1H), 8.47-8.40 (m, 2H), 7.96 (d, J=8.8 Hz, 1H), 7.79 (dd, J=8.6, 4.3 Hz, 1H), 4.91 (s, 2H). MS (DCI—NH3) m/z=161 (M+H)+, m/z=178 (M+NH4)+.

Provenance & Evidence