反应详情

温度

23 °C

A 40 mL vial cooled in a dry ice/acetone bath was charged with chlorodifluoromethane (0.209 g, 2.413 mmol) followed by the addition of 8-hydroxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde 398A (0.5 g, 2.413 mmol), Cs2CO3 (0.786 g, 2.413 mmol) and DMF (4.83 mL). The dry ice/acetone bath was removed; and with continued stirring, the reaction was slowly warmed to 23° C. After 2.5 hr, the reaction was transferred to a sand bath and stirred at 70° C. for 72 hr. The crude material was purified by prep HPLC-MS (30-55% MeCN in water, basic mode). The fractions were collected and concentrated in vacuo to give the title compound as a white solid (0.404 g, 57% yield): 1H NMR (400 MHz, DMSO-d6) δ ppm 1.44-1.51 (m, 3H) 4.93 (q, J=6.82 Hz, 1H) 7.08-7.28 (m, 1H) 7.32 (d, J=1.77 Hz, 1H) 7.46 (d, J=1.01 Hz, 1H) 9.83-9.88 (m, 1H) 11.14 (s, 1H). ESI-MS: m/z 258.1 (M+H)+.

1. temperatureA 40 mL vial cooled in a dry ice/acetone bath
2. customThe dry ice/acetone bath was removed
3. customthe reaction was transferred to a sand bath
4. customThe crude material was purified by prep HPLC-MS (30-55% MeCN in water, basic mode)
5. customThe fractions were collected
6. concentrationconcentrated in vacuo