Bromine → N-{4-[(3-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3,5-difluorophenyl}acetamide

HRID 2192149ノート

反応式

HRID 2192149 の反応式
[F:1][C:2]1[CH:3]=[C:4]([NH:19][C:20](=[O:22])[CH3:21])[CH:5]=[C:6]([F:18])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[NH:15][CH:16]=[CH:17][C:10]=12.[Br:23]Br>C(O)(=O)C.ClCCl>[Br:23][C:17]1[C:10]2[C:11](=[N:12][CH:13]=[CH:14][C:9]=2[O:8][C:7]2[C:6]([F:18])=[CH:5][C:4]([NH:19][C:20](=[O:22])[CH3:21])=[CH:3][C:2]=2[F:1])[NH:15][CH:16]=1

参加物

5

反応物 2

HCID 24408BromineHCID 59740995N-[3,5-Difluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]acetamide

生成物 1

HCID 59740988N-{4-[(3-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3,5-difluorophenyl}acetamide

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
10 °C

実験手順

1.05 g (3.45 mmol) of N-[3,5-difluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]acetamide are dissolved in 35 ml of glacial acetic acid and, using an ice bath, cooled to about 10° C. 4.8 ml (4.8 mmol) of a 1M solution of bromine in dichloromethane are added, and the mixture is stirred at 20° C. for about 30 min, resulting in the precipitation of a solid. The solid is filtered off with suction and washed with ethyl acetate. The mother liquor is neutralized using conc. aqueous sodium hydroxide solution and extracted with ethyl acetate. The crystals that were filtered off with suction are dissolved in 3 ml of DMF. The mixture is diluted with ethyl acetate and extracted three times with 1N sodium hydroxide solution. The combined organic phases are dried over magnesium sulfate. The solvent is removed under reduced pressure. The product is reacted without further purification.

後処理

  1. customresulting in the precipitation of a solid
  2. filtrationThe solid is filtered off with suction
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. filtrationThe crystals that were filtered off with suction
  6. dissolutionare dissolved in 3 ml of DMF
  7. additionThe mixture is diluted with ethyl acetate
  8. extractionextracted three times with 1N sodium hydroxide solution
  9. dry with materialThe combined organic phases are dried over magnesium sulfate
  10. customThe solvent is removed under reduced pressure
  11. customThe product is reacted without further purification

出典と根拠

ORDレコード
ord-a83bfafea191459ebbf3bfcdca39e61e
出典データセット
uspto-grants-2012_12
特許番号
US08329716B2

反応ノート

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