反応 #531822

反応方程式

2-[3-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-6-iodo-8-methyl-4H-3,1-benzoxazin-4-one

benzoxazinone

2-[3-chloro-1-(3-chloro-2-pyridin yl)-1H-pyrazol-5-yl]-6-iodo-8-methyl-4H-3,1-benzoxazin-4-one

copper(I) cyanide

→

title compound

2-[3-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-6-cyano-8-methyl-4H-3,1-benzoxazin-4-one

溶媒

ethyl acetate

tetrahydrofuran

反応条件

後処理

1. 1
   温度The reaction mixture was then heated
2. 2
   温度at reflux overnight
3. 3
   その他The reaction turned black in color, at which point thin layer chromatography on silica gel confirmed completion of the reaction
4. 4
   ろ過filtered through Celite®
5. 5
   洗浄by washing three times with 10% aqueous sodium bicarbonate solution
6. 6
   抽出The organic extract
7. 7
   乾燥was dried (MgSO4)
8. 8
   濃縮concentrated under reduced pressure

実験手順

To a solution of 2-[3-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-6-iodo-8-methyl-4H-3,1-benzoxazin-4-one (i.e. the benzoxazinone product of Step E) (600 mg; 1.2 mmol) in tetrahydrofuran (15 mL) was added copper(I) iodide (137 mg, 0.72 mmol), tetrakis(triphenyphosphine)palladium(0) (416 mg, 0.36 mmol) and copper(I) cyanide (860 mg, 9.6 mmol) sequentially at room temperature. The reaction mixture was then heated at reflux overnight. The reaction turned black in color, at which point thin layer chromatography on silica gel confirmed completion of the reaction. The reaction was diluted with ethyl acetate (20 mL) and filtered through Celite®, followed by washing three times with 10% aqueous sodium bicarbonate solution and once with brine. The organic extract was dried (MgSO4) and concentrated under reduced pressure to afford 397 mg of the title compound as a crude yellow solid.

出典