反应详情

温度

100 °C

To 3-fluoro-N-[4-methyl-3-(9H-pyrimido[4,5-b]indol-6-yl)phenyl]benzamide (205 mg, 0.517 mmol) was added 1,4-dioxane (3.1 mL) and aqueous sodium hydroxide (3.8M, 2.72 mL, 10.0 mmol) followed by solid sodium hydroxide (1.67 g, 41.7 mmol). The reaction was heated to 100° C. until LCMS indicated complete hydrolysis, typically 16-24 hours. The reaction was cooled to ambient temperature and partitioned between water and EtOAc, which resulted in the formation of solids. These solids were dissolved through successive extractions with EtOAc and 3:1 CHCl3:IPA. The organic phases were separately washed with water and saturated aqueous NaCl, then dried (MgSO4), the dried solutions were combined and evaporated to dryness to leave the crude product (133 mg, 93.8%). 1H NMR (300 MHz, DMSO): δ 12.33 (bs, 1H), 9.46 (s, 1H), 8.91 (s, 1H), 8.16 (s, 1H), 7.57 (d, 1H), 7.44 (dd, 1H), 6.94 (d, 1H), 6.4-6.6 (m, 2H), 5.00 bs, 2H), 2.08 (s, 3H). MS (EI) m/z=275 (M+H).

1. customhydrolysis, typically 16-24 hours
2. temperatureThe reaction was cooled to ambient temperature
3. custompartitioned between water and EtOAc, which
4. customresulted in the formation of solids
5. washThe organic phases were separately washed with water and saturated aqueous NaCl
6. dry with materialdried (MgSO4)
7. customevaporated to dryness