Water → Propane-1-sulfonic acid {3-[(5-bromo-1H-pyrrolo[2,3-b]-pyridin-3-yl)-hydroxy-methyl]-2-fluoro-phenyl}-amide

HRID 1261049노트

반응식

HRID 1261049 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.[F:11][C:12]1[C:17]([CH:18]=[O:19])=[CH:16][CH:15]=[CH:14][C:13]=1[NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22].[OH-].[K+].O>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:18]([OH:19])[C:17]3[C:12]([F:11])=[C:13]([NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22])[CH:14]=[CH:15][CH:16]=3)=[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 58086814Propane-1-sulfonic acid (2-fluoro-3-formyl-phenyl)-amide

생성물 1

HCID 58086504Propane-1-sulfonic acid {3-[(5-bromo-1H-pyrrolo[2,3-b]-pyridin-3-yl)-hydroxy-methyl]-2-fluoro-phenyl}-amide수율 45.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To 5-bromo-7-azaindole 67 (312 mg, 1.58 mmol) in methanol (28 mL) were added propane-1-sulfonic acid (2-fluoro-3-formyl-phenyl)-amide (503, 370 mg, 1.5 mmol) and potassium hydroxide (422.8 mg, 7.5 mmol) under an atmosphere of nitrogen. The reaction was stirred at room temperature overnight, then 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 20% ethyl acetate in hexane to give the desired compound as white solid (504, 300 mg, 45.0%).

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 20% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-3122c7d8ec5349b5a3e294e6ef74e006
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470818B2

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