Water → 7-bromo-3-(3-chlorophenyl)-2-methylisoquinolin-1(2H)-one

HRID 77389

反応式

HRID 77389 の反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[H-].[Na+].[N+]([C:25]1C=CC(S(OC)(=O)=O)=CC=1)([O-])=O.O>C1COCC1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[N:8]([CH3:25])[C:9]2=[O:12])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 22582Methyl-4-nitrobenzenesulfonateHCID 24758Sodium hydrideHCID 699288937-bromo-3-(3-chlorophenyl)isoquinolin-1(2H)-one2 回

生成物 1

HCID 699285487-bromo-3-(3-chlorophenyl)-2-methylisoquinolin-1(2H)-one収率 50.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

7-Bromo-3-(3-chlorophenyl)isoquinolin-1(2H)-one (Intermediate 23A) (0.1 g, 0.299 mmol) was dissolved in THF (4 mL), under an atmosphere of nitrogen. Sodium hydride (0.018 g, 0.448 mmol) was added and reaction stirred for 30 minutes. The reaction was then cooled using an ice bath and methyl 4-nitrobenzenesulfonate (0.065 g, 0.299 mmol) was added. The reaction was allowed to warm to room temperature and left to stir overnight. Water was added to the reaction mixture and extracted with EtOAC (×2). The organics were combined and washed with brine, dried (MgSO4) filtered and concentrated under reduced pressure. The mixture was purified on silica (25 g column on Isolera 4) eluting with 0-10% methanol in dichloromethane to afford 7-bromo-3-(3-chlorophenyl)-2-methylisoquinolin-1(2H)-one (51 mg, 0.15 mmol).

後処理

  1. customreaction
  2. temperatureThe reaction was then cooled
  3. waitleft
  4. stirringto stir overnight
  5. extractionextracted with EtOAC (×2)
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe mixture was purified on silica (25 g column on Isolera 4)
  11. washeluting with 0-10% methanol in dichloromethane

出典と根拠

ORDレコード
ord-d964deca7655450c9db475cc20959061
出典データセット
uspto-grants-2014_09
特許番号
US08841289B2

関連ノート

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