Potassium Carbonate → HCID 58042385、化合物

HRID 2048084ノート

反応式

HRID 2048084 の反応式
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:9](F)=[CH:10][C:11]([F:21])=[C:12]([CH:20]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[Cl:23][C:24]1[CH:25]=[C:26]([OH:38])[CH:27]=[N:28][C:29]=1[O:30][CH2:31][C:32]([F:37])([F:36])[CH:33]([F:35])[F:34].COC(C)(C)C>CS(C)=O>[Cl:7][C:8]1[C:9]([O:38][C:26]2[CH:27]=[N:28][C:29]([O:30][CH2:31][C:32]([F:36])([F:37])[CH:33]([F:35])[F:34])=[C:24]([Cl:23])[CH:25]=2)=[CH:10][C:11]([F:21])=[C:12]([CH:20]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 15413tert-Butyl methyl etherHCID 580423945-Chloro-6-(2,2,3,3-tetrafluoropropoxy)pyridin-3-olHCID 58042499Tert-butyl 5-chloro-2,4-difluorobenzoate

生成物 1

HCID 58042385HCID 58042385、化合物収率 61%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Potassium carbonate (3.02 g, 21.85 mmol) was added portionwise to a suspension of tert-butyl 5-chloro-2,4-difluorobenzoate (Preparation 59, 2.26 g, 9.09 mmol), 5-chloro-6-(2,2,3,3-tetrafluoropropoxy)pyridin-3-ol (Preparation 73, 2.25 g, 8.67 mmol) in DMSO (13.5 mL). The mixture was stirred at room temperature under nitrogen for 3 hours. tert-butyl methyl ether (50.0 mL) was added and the mixture was washed with water (3×50.0 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting oil was suspended with heptane (20.0 mL) and concentrated in vacuo. The resulting solid was suspended in heptane (20.0 mL) and heated to 90° C. until full dissolution. The mixture was cooled with stirring and the residual solid collected by filtration. The filtrate was concentrated in vacuo and the resulting solid was suspended in heptane (10.0 mL) and heated to 90° C. until dissolution. The mixture was again cooled with stirring and the residual solid collected by filtration. The two crops were combined to yield the title compound as a white solid (2.58 g, 5.29 mmol, 61%):

後処理

  1. washthe mixture was washed with water (3×50.0 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. concentrationconcentrated in vacuo
  6. temperatureheated to 90° C. until full dissolution
  7. temperatureThe mixture was cooled
  8. stirringwith stirring
  9. filtrationthe residual solid collected by filtration
  10. concentrationThe filtrate was concentrated in vacuo
  11. temperatureheated to 90° C. until dissolution
  12. temperatureThe mixture was again cooled
  13. stirringwith stirring
  14. filtrationthe residual solid collected by filtration

出典と根拠

ORDレコード
ord-1aaa9902cbb2402f9a3e1bd58b355198
出典データセット
uspto-grants-2013_11
特許番号
US08592629B2

反応ノート

読み込み中…