Water → (5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-[6-chloro-2-fluoro-3-(2,2,2-trifluoro-ethoxy)-phenyl]-methanol

HRID 1098510노트

반응식

HRID 1098510 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[Cl:11][C:12]1[C:17]([CH:18]=[O:19])=[C:16]([F:20])[C:15]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:14][CH:13]=1.[OH-].[K+].O>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:18]([C:17]3[C:12]([Cl:11])=[CH:13][CH:14]=[C:15]([O:21][CH2:22][C:23]([F:25])([F:26])[F:24])[C:16]=3[F:20])[OH:19])=[CH:6][NH:7][C:8]2=[N:9][CH:10]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 595068296-Chloro-2-fluoro-3-(2,2,2-trifluoro-ethoxy)-benzaldehyde

생성물 1

HCID 59506814(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-[6-chloro-2-fluoro-3-(2,2,2-trifluoro-ethoxy)-phenyl]-methanol

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To 5-bromo-7-azaindole (67, 291 mg, 1.48 mmol) in methanol (22 mL) were added 6-Chloro-2-fluoro-3-(2,2,2-trifluoro-ethoxy)-benzaldehyde (523, 400.0 mg, 1.6 mmol) and potassium hydroxide (1.49 g, 26.6 mmol) under an atmosphere of nitrogen. The reaction was stirred at room temperature for 48 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 25% ethyl acetate in hexane to give the compound (524, 300 mg, 42%). MS (ESI) [M+H+]+=453.1, 455.1.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 25% ethyl acetate in hexane
  7. customto give the compound (524, 300 mg, 42%)

출처 및 근거

ORD 기록
ord-148bad5f7c85452e976131a0354b9e4b
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143271B2

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