反应详情

温度

80 °C

To a solution of 5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide (30 mg, 0.10 mmol) in DMF (5.0 mL) was added K2CO3 (28 mg, 0.20 mmol), followed by 2-(2-fluoro-5-nitrophenyl)ethanol (37 mg, 0.20 mmol). The mixture was warmed to 80° C. stirred for about 16 hr. After cooling down to RT, the mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (15 mL) and water (15 mL), the aqueous was extracted with ethyl acetate (3×10 mL). The combined organic phases were washed brine (10 mL), dried over Na2SO4, filtered, concentrated and purified by Pre-TLC (DCM/CH3OH=20/1) to afford the product about 5.0 mg (11.1%). 1H NMR (400 MHz, DMSO-d6) δ 8.35 (t, J=4.0 Hz, 1 H), 8.28 (d, J=2.8 Hz, 1 H), 8.22 (dd, J=2.8, 9.2 Hz, 1 H), 8.12 (d, J=9.2 Hz, 1 H), 7.64-7.60 (m, 2 H), 7.45-7.41 (m, 2 H), 7.22-7.17 (m, 1 H), 7.14-7.09 (m, 4 H), 3.72-3.65 (m, 2 H), 3.29-3.24 (m, 2 H). MS (ESI) m/e [M+1]+ 442.

1. temperatureAfter cooling down to RT
2. concentrationthe mixture was concentrated under reduced pressure
3. customThe residue was partitioned between ethyl acetate (15 mL) and water (15 mL)
4. extractionthe aqueous was extracted with ethyl acetate (3×10 mL)
5. washThe combined organic phases were washed brine (10 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. custompurified by Pre-TLC (DCM/CH3OH=20/1)