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

HRID 1497397
ノート
印刷プレビュー

反応式

HRID 1497397 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ef280576491a457fa7a1eb89ec9bcaa9
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09199963B2

反応ノート

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