Potassium Hydroxide → 4-((1H-Pyrrolo[2,3-B]pyridin-4-YL)oxy)-3-fluoroaniline

HRID 16405

反応式

HRID 16405 の反応式
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[F:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[OH:19])[NH2:15].[OH-].[K+]>O>[F:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[O:19][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12)[NH2:15]

参加物

5

反応物 3

HCID 14797Potassium Hydroxide2 回HCID 2735918Phenol, 4-amino-2-fluoro-2 回HCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 160379654-((1H-Pyrrolo[2,3-B]pyridin-4-YL)oxy)-3-fluoroaniline

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

543 mg (3.56 mmol) of 4-chloro-1H-pyrrolo[2,3-b]pyridine (from example XVIII, 905 mg (7.12 mmol) of 3-fluoro-4-hydroxyaniline and 399 mg (7.12 mmol) of powdered potassium hydroxide are heated at 260° C. for 8 hours. Another 905 mg (7.12 mmol) of 3-fluoro-4-hydroxyaniline and 200 mg (3.56 mmol) of powdered potassium hydroxide are added, and the mixture is reacted at 260° C. for another 8 h. For work-up, the mixture is cooled to room temperature, diluted with water and extracted three times with ethyl acetate. The organic phase is dried over magnesium sulfate and concentrated using a rotary evaporator. The residue is purified by preparative HPLC. The fractions which, according to LC-MS, contain 39% of product are used without further purification for the next reaction.

後処理

  1. customthe mixture is reacted at 260° C. for another 8 h
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated
  5. customa rotary evaporator
  6. customThe residue is purified by preparative HPLC
  7. customare used without further purification for the next reaction

出典と根拠

ORDレコード
ord-e1ae06632b2441b793d7925135e5427b
出典データセット
uspto-grants-2010_06
特許番号
US07737153B2

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