反应详情

温度

93 °C

To a stirred solution of 3-(4-fluorobenzoyl)-8-(3-methoxyphenyl)-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester (48 mg, 0.10 mmol) in 2 mL of EtOH was added 0.30 mL of 1M Na2CO3 solution at ambient temperature. The reaction mixture was heated at 93° C. reflux under N2for 3.5 hours and samples monitored by LC-MS. The solution was diluted with DCM (10 mL), washed with brine. The aqueous phase was extracted with DCM (10 mL) twice. The combined organic phase was dried over Na2SO4 and concentrated. The crude product was purified by flash chromatograph on silica gel, eluting with EtOAc-hexane (0-30%) to yield the title compound (33 mg) as a yellow solid; 1H-NMR (CDCl3): δ 10.46 (1H, s), 7.73 (1H, d), 7.47 (1H, d), 7.37 (1H, d), 7.26 (2H, m), 7.12 (1H, m), 7.00 (1H, m), 6.79 (1H, m), 5.25 (1H, s), 4.21(2H, m), 3.80 (3H, s), 3.55 (2H, m), 3.11 (2H, m), 1.26 (3H, t). MS (ESI): 363 (MH+).

1. temperaturereflux under N2for 3.5 hours and samples
2. washwashed with brine
3. extractionThe aqueous phase was extracted with DCM (10 mL) twice
4. dry with materialThe combined organic phase was dried over Na2SO4
5. concentrationconcentrated
6. customThe crude product was purified by flash chromatograph on silica gel
7. washeluting with EtOAc-hexane (0-30%)