反应详情

To a solution of 5-aminobenzo[f][1,7]naphthyridine-8-carbaldehyde (from Example 87) (1.0 eq.) in THF (0.02M) was added MeLi (2.5 eq.) at −78° C. The reaction was allowed to warm to ambient temperature overnight. The reaction was quenched by saturated NH4Cl and extracted with EtOAc. 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 0-5% MeOH/DCM to give 145-aminobenzo[f][1,7]naphthyridin-8-yl)ethanol as a yellow solid: 1H NMR (methanol-d4): δ 8.94 (dd, 1H), 8.88 (dd, 1H), 8.38 (d, 1H), 7.81 (dd, 1H), 7.62 (d, 1H), 7.41 (dd, 1H), 4.97 (q, 1H), 1.53 (d, 3H). LRMS [M+H]=240.1.

1. customThe reaction was quenched by saturated NH4Cl
2. extractionextracted with EtOAc
3. washThe combined organic layer was washed with brine
4. dry with materialdried over MgSO4
5. concentrationconcentrated en vacuo
6. customto obtain a crude residue
7. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)
8. customto give 145-aminobenzo[f][1,7]naphthyridin-8-yl)ethanol as a yellow solid