反应详情

5-Dibromomethyl-pyrazine-2-carboxylic acid methyl ester. 5-Methyl-pyrazine-2-carboxylic acid methyl ester (1.60 g, 10.5 mmol; Macdonald, S. J. F. et al. J. Med. Chem. 2002, 45(18):3878-3890.), N-bromosuccinimide (5.62 g, 31.6 mmol), and dibenzoyl peroxide (0.255 g, 1.05 mmol) were dissolved in CCl4 (80 mL). The mixture was heated at reflux for 18 h. The reaction mixture was cooled and washed with 10% aq. Na2SO3 (2×20 mL) and H2O (1×30 mL). The organic phase was dried over Na2SO4, filtered, and concentrated to yield a brown oily crude material (2.41 g). The crude product was purified (SiO2: 0-20% ethyl acetate/hexanes) to give the title compound (1.00 g, 31%).

1. temperatureThe mixture was heated
2. temperatureat reflux for 18 h
3. temperatureThe reaction mixture was cooled
4. washwashed with 10% aq. Na2SO3 (2×20 mL) and H2O (1×30 mL)
5. dry with materialThe organic phase was dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customto yield a brown oily crude material (2.41 g)
9. customThe crude product was purified (SiO2: 0-20% ethyl acetate/hexanes)