反应详情

温度

100 °C

The alcohol 1h (15 mg) was dissolved in dry DCE and 20 mg of sodium bicarbonate was added, followed by 2 ml of a phosgene solution in toluene (20%). The reaction mixture was stirred at room temperature for 3 h (full conversion to chloroimidate according to LC-MS) and then concentrated by rotary evaporation and dried from excess of phosgene in high vacuum (1.5 h). The dry reaction mixture was transferred into a “microwave” vial (2-5 ml), mixed with dry DCE (3 ml), 3-amino-5-methoxy-benzonitrile (2 eq), potassium carbonate (9 mg, 1.5 eq), pulverized molecular sieves (4 Å, 5 mg) and heated in a microwave at 100° C. for 45 min. The reaction mixture was passed through short pad of silica (eluent DCM, then 10% methanol in DCM). The resulting fractions containing the desired carbamate compound were combined, concentrated by rotary evaporation and purified by column chromatography on YMC silica (15 g, ethyl acetate/petroleum ether 1:3 to remove excess of aniline, followed by dichloromethane and then 2% methanol in dichloromethane) to give the title compound as a powder (15 mg, 8%), [M+H]+ 628.

1. concentrationconcentrated by rotary evaporation
2. dry with materialdried from excess of phosgene in high vacuum (1.5 h)
3. customThe dry reaction mixture
4. concentrationconcentrated by rotary evaporation
5. custompurified by column chromatography on YMC silica (15 g, ethyl acetate/petroleum ether 1:3
6. customto remove excess of aniline