反应 #992704

反应方程式

methanesulfonyl chloride

3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid

5-chloro-7-methylindoline-2,3-dione

3-picoline

→

title product

收率 77.6%

1-[[3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]carbonyl]-5-chloro-7-methyl-1H-indole-2,3-dione

收率 77.6%

溶剂

acetonitrile

反应条件

后处理

1. 1
   温度the mixture was warmed to room temperature for 20 hours
2. 2
   过滤The precipitated solids were filtered
3. 3
   洗涤washed with acetonitrile (3×5 mL)
4. 4
   其他dried under nitrogen

实验过程

To a suspension of 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid (see PCT Patent Publication WO 03/015519 for preparation) (97.6% purity, 13.02 g, 42 mmol) and 5-chloro-7-methylindoline-2,3-dione (K. Tsuji et al., Bioorg. Med. Chem. Letters, 2002, 12(17), pp 2427-2430) (7.82 g, 40 mmol) in dry acetonitrile (50 mL) was added 3-picoline (11.9 g, 127 mmol). The mixture was cooled to 0° C., and then methanesulfonyl chloride (6.87 g, 60 mmol) was added dropwise at 0-10° C. After stirring 5 minutes at this temperature, the mixture was warmed to room temperature for 20 hours. The precipitated solids were filtered, washed with acetonitrile (3×5 mL), and dried under nitrogen to afford the title product, a compound of the present invention, as a yellow powder, 14.90 g (77.6% yield), m.p. 173-177° C. (decomp.).

来源