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Phosphorus oxybromide → 4-bromo-1-(2-ethyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-one

HRID 1497397
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HRID 1497397 반응식
[CH2:1]([N:3]1[C:11]([CH3:12])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:13]3[CH:18]=[CH:17][C:16](O)=[CH:15][C:14]3=[O:20])=[CH:9]2)=[N:4]1)[CH3:2].P(Br)(Br)([Br:23])=O.C(=O)([O-])O.[Na+]>CN(C)C=O>[Br:23][C:16]1[CH:17]=[CH:18][N:13]([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[C:11]([CH3:12])[N:3]([CH2:1][CH3:2])[N:4]=3)[CH:9]=2)[C:14](=[O:20])[CH:15]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 1177986361-(2-ethyl-3-methyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one

생성물 1

HCID 1177987484-bromo-1-(2-ethyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-one수율 51.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To a solution of 1-(2-ethyl-3-methyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one (1.07 g) in N,N-dimethylformamide (20 ml) was added phosphorus oxybromide (1.37 g) at room temperature, and the mixture was stirred at 50° C. overnight. The reaction mixture was cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was recrystallized from ethanol-hexane to give the title compound (680 mg).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was recrystallized from ethanol-hexane

출처 및 근거

ORD 기록
ord-ef280576491a457fa7a1eb89ec9bcaa9
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09199963B2

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