反应详情

温度

80 °C

4-Nitro-1H-pyrazole (118 mg, 1.02 mmol, 1.0 eq) is added at room temperature to a stirred solution of 3-bromomethyl-6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthrene (350 mg, 1.02 mmol, 1.0 eq) in N,N-dimethylformamide (12 mL), followed by N,N-diisopropylethylamine (196 μL, 1.12 mmol, 1.1 eq). After 24 hours stirring at 80° C., solvent is removed and the residue is extracted with dichloromethane (3×20 mL) and water (20 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by column chromatography (silica gel, eluent: cyclohexane:ethyl acetate, 1:1 to 0:1, v/v) to afford 6-methoxy-3-(4-nitro-pyrazol-1-ylmethyl)-3,4-dihydro-2H-1-oxa-9-aza-phenanthrene as a light yellow viscous oil (222 mg, 61% yield).

1. customsolvent is removed
2. extractionthe residue is extracted with dichloromethane (3×20 mL) and water (20 mL)
3. dry with materialThe combined organic layers are dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customto give a residue that
7. customis purified by column chromatography (silica gel, eluent