反応 #1383725
ord-064c8d7cd1a54c2fb1132ec2479efdae
反応方程式
反応物
試薬
反応条件
後処理
- 1workup.STIRRINGstirring
- 2workup.WAITwas continued for an additional 5 minutes
- 3その他the temperature below 5° C
- 4workup.STIRRINGThe reaction mixture was stirred 40 minutes at 0° C.
- 5温度The reaction mixture was then warmed to room temperature
- 6workup.STIRRINGstirred overnight
- 7抽出extracted with ethyl acetate (3×50 mL)
- 8洗浄The combined ethyl acetate extracts were washed successively with 10% aqueous sodium bicarbonate (1×20 mL) and brine (1×20 mL)
- 9乾燥dried (MgSO4)
- 10濃縮concentrated under reduced pressure
- 11その他The residual solid was purified by chromatography on silica gel
実験手順
To a solution of methanesulfonyl chloride (0.31 mL, 4.07 mmol) in acetonitrile (10 mL) was added dropwise a mixture of 3-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid (i.e. the carboxylic acid product of Example 3, Step D) (1.0 g, 3.87 mmol) and triethylamine (0.54 mL, 3.87 mmol) in acetonitrile (5 mL) at 0° C. The reaction mixture was then stirred for 15 minutes at 0° C. Then, 2-amino-3-chloro-5-iodobenzoic acid (i.e. the product from Step A) (1.15 g, 3.87 mmol) was added, and stirring was continued for an additional 5 minutes. A solution of triethylamine (1.08 mL, 7.74 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 (0.31 mL, 4.07 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 under reduced pressure. The residual solid was purified by chromatography on silica gel to afford 575 mg of the title compound as a crude yellow solid.