反应 #8607

反应方程式

ethyl disulfide

water

4-[5-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-phenyl-2-pyrimidinamine

n-butyllithium

→

N-{4-[5-chloro-7-(ethylsulfanyl)-2-(4fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-pyrimidinyl}-N-phenylamine

收率 22.1%

溶剂

ethyl acetate

tetrahydrofuran

反应条件

后处理

1. 1
   其他The phases were separated
2. 2
   洗涤the ethyl acetate phase was washed with water
3. 3
   干燥dried (magnesium sulfate)
4. 4
   过滤filtered
5. 5
   浓缩concentrated
6. 6
   其他The resulting residue was crystallized from acetonitrile

实验过程

To a solution of 4-[5-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-phenyl-2-pyrimidinamine (80 mg, 0.19 mmol) in tetrahydrofuran (5 mL) was added n-butyllithium (0.43 mL of 1.6M solution in hexane, 0.67 mmol) at −78° C. The resulting dark solution was stirred for 10 minutes, then quenched by the addition of ethyl disulfide (0.08 mL 6.5 mmol). The reaction mixture was allowed to warm to room temperature, then water and ethyl acetate were added. The phases were separated and the ethyl acetate phase was washed with water, dried (magnesium sulfate), filtered and concentrated. The resulting residue was crystallized from acetonitrile to give N-{4-[5-chloro-7-(ethylsulfanyl)-2-(4fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-pyrimidinyl}-N-phenylamine (20 mg, 22%) as a solid. 1H NMR (CDCl3): δ 8.30 (d, 1H), 8.22 (d, 1H), 7.66 (m, 3H), 7.40 (t, 2H), 7.1–7.24 (m, 4H), 6.75 (d, 1H), 6.52 (d, 1 H), 3.20 (q, 2H), 1.54 (t, 3H); 19F-NMR (CDCl3): δ −112.55; MS m/z 476 (M+1).

来源