Chloroacetone → 1-(6-Bromo-5-(2,4-difluorophenoxy)-1H-indazol-1-yl)propan-2-one

HRID 912473ノート

反応式

HRID 912473 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[O:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:27][C:28](=[O:30])[CH3:29]>CN(C=O)C.O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:27][C:28](=[O:30])[CH3:29])=[CH:4][C:3]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19]

参加物

6

反応物 3

HCID 6571ChloroacetoneHCID 10796Cesium carbonateHCID 574187616-Bromo-5-(2,4-difluorophenoxy)-1H-indazole

生成物 1

HCID 674168791-(6-Bromo-5-(2,4-difluorophenoxy)-1H-indazol-1-yl)propan-2-one収率 69%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 6-bromo-5-(2,4-difluorophenoxy)-1H-indazole (prepared according to Example 16, Steps A-D; 10.07 g, 31.0 mmol) in DMF (150 mL) at ambient temperature was added cesium carbonate (30.3 g, 92.9 mmol), followed by chloroacetone (5.2 mL, 65.1 mmol). The resulting mixture was vigorously stirred at ambient temperature for 1 hr, then diluted with water (1000 mL). After stirring for 1 hr, the precipitate that formed was collected by filtration, washed with water, and air-dried. This material was dissolved in boiling ethanol (150 mL), and then of water (80 mL) was added. The resulting mixture was cooled at 2° C. for 16 hr. The crystals that formed were collected by filtration, washed with 50/50 water/ethanol, and dried under vacuum to afford the title compound as a light orange powder (8.13 g, 69%).

後処理

  1. stirringAfter stirring for 1 hr
  2. customthe precipitate that formed
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customair-dried
  6. dissolutionThis material was dissolved
  7. additionof water (80 mL) was added
  8. temperatureThe resulting mixture was cooled at 2° C. for 16 hr
  9. customThe crystals that formed
  10. filtrationwere collected by filtration
  11. washwashed with 50/50 water/ethanol
  12. customdried under vacuum

出典と根拠

ORDレコード
ord-fab0902815bc4b6895f46522ed46be9f
出典データセット
uspto-grants-2011_09
特許番号
US08026233B2

反応ノート

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