반응 #531822

반응 방정식

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

용매

ethyl acetate

tetrahydrofuran

반응 조건

후처리

1. 1
   온도The reaction mixture was then heated
2. 2
   온도at reflux overnight
3. 3
   기타The reaction turned black in color, at which point thin layer chromatography on silica gel confirmed completion of the reaction
4. 4
   여과filtered through Celite®
5. 5
   세척by washing three times with 10% aqueous sodium bicarbonate solution
6. 6
   추출The organic extract
7. 7
   건조was dried (MgSO4)
8. 8
   농축concentrated under reduced pressure

실험 절차

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.

출처