反应 #531826
ord-bad644d90fb74bf7831def9e79a985b0
反应方程式
反应物
试剂
反应条件
后处理
- 1workup.STIRRINGstirring
- 2workup.WAITwas continued for an additional 5 minutes
- 3其他the temperature below 5° C
- 4workup.STIRRINGThe reaction mixture was stirred
- 5温度The reaction mixture was then warmed to room temperature
- 6workup.STIRRINGstirred overnight
- 7萃取extracted with ethyl acetate (3×50 mL)
- 8洗涤The combined ethyl acetate extracts were washed successively with 10% aqueous sodium bicarbonate (1×20 ml) and brine (1×20 mL)
- 9干燥dried (MgSO4)
- 10浓缩concentrated
实验过程
To a solution of methanesulfonyl chloride (0.54 ml, 6.94 mmol) in acetonitrile (15 mL) was added dropwise a mixture of 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid (i.e. the carboxylic acid product of Step D) (2.0 g, 6.6 mmol) and triethylamine (0.92 ml, 6.6 mmol) in acetonitrile (5 mL) at 0° C. The reaction mixture was then stirred for 15 minutes at 0° C. Then, 2-amino-3-methyl-5-iodobenzoic acid (i.e. the product from Example 1, Step A) (1.8 g, 6.6 mmol) was added, and stirring was continued for an additional 5 minutes. A solution of triethylamine (1.85 mL, 13.2 mmol) in acetonitrile (5 mL) was then added dropwise while keeping the temperature below 5° C. The reaction mixture was stirred. 40 minutes at 0° C., and then methanesulfonyl chloride (0.54 ml, 6.94 mmol) was added. The reaction mixture was then warmed to room temperature and stirred overnight. The reaction mixture was then diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined ethyl acetate extracts were washed successively with 10% aqueous sodium bicarbonate (1×20 ml) and brine (1×20 mL), dried (MgSO4) and concentrated to afford 2.24 g of the title product as a crude yellow solid.