Sodium borohydride → 7-Bromo-1,2,3,4-tetrahydro-1,8-naphthyridin-4-ol

Participants

Reaction Conditions

Reaction Steps

A solution of 7-bromo-2,3-dihydro-1,8-naphthyridin-4(1H)-one (500 mg, 2.20 mmol) in THF (15 ml) was treated with NaBH4 (167 mg, 4.40 mmol) and stirred at 25° C. for 2 h. The reaction mixture was quenched with sat. aq. NH4Cl and extracted 2× with DCM. The org layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude material was purified by normal phase chromatography (12 g silica gel cartridge, heptanes/EtOAc 100:0 to 50:50) to give the title compound as a white solid. (UPLC-MS 3) tR 0.59; ESI-MS 229.0, 231.0 [M+H]+.

Provenance & Evidence