反应详情

温度

100 °C

9-bromo-4-iodo-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one (100 mg, 0.20 mmol), acetic hydrazide (16.3 mg, 0.220 mmol), Mo(CO)6 (52.8 mg, 0.200 mmol), t-butylphosphine HBF4 salt (5.80 mg, 0.020 mmol), and trans-di-mu-acetatobis[2-(di-o-tolylphosphino)benzyl]dipalladium(II) (9.38 mg, 10.00 mmol) were added to a microwave vial and flushed with nitrogen. Dioxane (2000 μl) was added followed by Hunig's base (34.9 μl 0.200 mmol) and degassed for 10 min with subsurface N2 bubbling. The reaction flask was then sealed and heated to 100° C. for 2 h. The crude reaction mixture was then diluted with DMSO and purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.05% TFA, to give the title compound as a white solid and also N′-acetyl-9-bromo-1-oxo-6-[(1,2,2-trimethylpropyl)amino]-1,2-dihydrobenzo[c]-1,6-naphthyridine-4-carbohydrazide as a white solid. 1H NMR (500 MHz, CD3OD) δ 11.88 (d, 1H, J=6.0 Hz), 10.14 (d, 1H, J=2.0 Hz), 10.03 (d, 1H, J=4.0 Hz), 8.56 (d, 1H, J=9.0 Hz), 8.20 (d, 1H, J=7.0 Hz), 7.85 (m, 3H), 4.21 (m, 1H), 1.22 (d, 3H, J=13.5 Hz), 0.96 (s, 9H). LRMS (ESI) calc'd for (C19H22BrN4O2) [M+H]+, 417.1; found 417.0.

1. customflushed with nitrogen
2. additionDioxane (2000 μl) was added
3. customdegassed for 10 min with subsurface N2 bubbling
4. customThe reaction flask was then sealed
5. customThe crude reaction mixture
6. custompurified by preparative HPLC Reverse phase (C-18)
7. washeluting with Acetonitrile/Water+0.05% TFA