反应详情

温度

80 °C

To a solution of methyl 5-aminobenzo[f][1,7]naphthyridine-8-carboxylate (from the previous step) (1.0 eq.) in EtOH (0.03M) was added NaBH4 (10 eq.) at 25° C. The solution was heated to 80° C. for 5 hours. After cooling to ambient temperature, the reaction mixture was concentrated en vacuo. The residue was portionized between saturated NaHCO3 and EtOAc. The layers were separated and aqueous layer was extracted with EtOAc twice. The combined organic layer was washed with brine, dried over MgSO4 and concentrated en vacuo to obtain a crude residue. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-10% MeOH/DCM to give (5-aminobenzo[f][1,7]naphthyridin-8-yl)methanol as an off white solid: 1H NMR (methanol-d4): δ 8.82 (dd, 1H), 8.77 (dd, 1H), 7.26 (d, 1H), 7.70 (dd, 1H), 7.50 (d, 1H), 7.27 (dd, 1H), 4.66 (s, 2H). LRMS [M+H]=226.1.

1. temperatureAfter cooling to ambient temperature
2. concentrationthe reaction mixture was concentrated en vacuo
3. customThe layers were separated
4. extractionaqueous layer was extracted with EtOAc twice
5. washThe combined organic layer was washed with brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated en vacuo
8. customto obtain a crude residue
9. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)