反应详情

温度

70 °C

As illustrated in the scheme above, a mixture of 4-(dimethylamino)-1-naphthalenecarboxylic acid (0.1 mmol), diphenylphosphoryl azide (0.15 mmol) and triethylamine (0.3 mmol) in toluene (10 ml) was heated at reflux overnight. The solvent was evaporated in vacuo, and then the residue was redissolved in dichloroethane, added to INTERMEDIATE 1 (0.08 mmol) and heated at 70° C. for 4 hours. The solvent was evaporated in vacuo and the residue was taken in dichloromethane (50 ml). The organic phase was washed with brine (2×10 ml); the organic phase was dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with ether and the title compound was obtained as a colorless solid (9 mg, 22%); 1H-NMR (CDCl3): δ 8.27 (m, 1H), 8.11 (m, 1H), 7.60 (d, J=8 Hz, 1H), 7.77-7.29 (m, 10H), 7.08 (d, J=8.4 Hz, 1H), 6.75 (br s, 2H), 5.56 (d, J=8.4 Hz, 1H), 3.39 (s, 3H) and 2.90 (s, 6H); MS (ESI) (M+H)+=512.

1. temperaturewas heated
2. temperatureat reflux overnight
3. customThe solvent was evaporated in vacuo
4. dissolutionthe residue was redissolved in dichloroethane
5. customThe solvent was evaporated in vacuo
6. washThe organic phase was washed with brine (2×10 ml)
7. dry with materialthe organic phase was dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was triturated with ether