1,2-Difluoro-4-nitrobenzene → 6-bromo-5-(2-fluoro-4-nitrophenoxy)-1H-indazole

HRID 1661971ノート

反応式

HRID 1661971 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[OH:11].[F:12][C:13]1[CH:14]=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=[CH:17][C:18]=1F.C([O-])(O)=O.[Na+].[Li+].[Cl-]>CN(C=O)C.C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[O:11][C:18]1[CH:17]=[CH:16][C:15]([N+:20]([O-:22])=[O:21])=[CH:14][C:13]=1[F:12]

参加物

7

反応物 4

HCID 1230531,2-Difluoro-4-nitrobenzeneHCID 433294Lithium ChlorideHCID 516892Sodium BicarbonateHCID 591599466-Bromo-1H-indazol-5-ol

生成物 1

HCID 667671536-bromo-5-(2-fluoro-4-nitrophenoxy)-1H-indazole収率 50.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

A mixture of 6-bromo-5-hydroxy-1H-indazole (7.0 g, 33.0 mmol), 3,4-difluoronitrobenzene (4.98 mg, 31.0 mmol), NaHCO3 (2.5 g, 31.0 mmol) in DMF (100 mL) is stirred at 80° C. for 4 hours. Then LiCl (10% aqueous solution) is added and the solution is extracted with EtOAc. The organic phase is dried over anhydrous MgSO4, filtered and concentrated. The residue is purified by silica gel column chromatography eluting with PE:DCM (1:1) to give the desired product (5.5 g, 46.6% yield). MS (m/z): 354.0 (M+H).

後処理

  1. extractionthe solution is extracted with EtOAc
  2. dry with materialThe organic phase is dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel column chromatography
  6. washeluting with PE

出典と根拠

ORDレコード
ord-2834e9e657a443aabaa3f6184b648543
出典データセット
uspto-grants-2011_10
特許番号
US08030302B2

反応ノート

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