4-Fluorobenzoyl chloride → N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluorobenzamide

HRID 1923734

Reaktionsgleichung

Reaktionsgleichung von HRID 1923734
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Br:11][C:12]1[C:13]([F:22])=[C:14]2[C:20]([NH2:21])=[CH:19][NH:18][C:15]2=[N:16][CH:17]=1>N1C=CC=CC=1>[Br:11][C:12]1[C:13]([F:22])=[C:14]2[C:20]([NH:21][C:6](=[O:7])[C:5]3[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:19][NH:18][C:15]2=[N:16][CH:17]=1

Komponenten

4

Edukt 2

HCID 678794-Fluorobenzoyl chlorideHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Produkt 1

HCID 60205349N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluorobenzamideAusbeute 78,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

4-Fluorobenzoyl chloride (0.15 mL, 1.30 mmol) was added to 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (200 mg, 0.87 mmol, Example 1, Step H) in pyridine (5 mL). The reaction was stirred at room temperature for 10 minutes, and then the pyridine was removed. THF (5 mL) and 2N LiOH (3 mL) were added and stirred for 20 minutes. The THF was removed, and water (20 mL) was added. The solid formed was collected by filtration and dried to give N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluorobenzamide (0.24 g, 77% yield) as a solid.

Aufarbeitung

  1. customthe pyridine was removed
  2. additionTHF (5 mL) and 2N LiOH (3 mL) were added
  3. stirringstirred for 20 minutes
  4. customThe THF was removed
  5. additionwater (20 mL) was added
  6. customThe solid formed
  7. filtrationwas collected by filtration
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3636d7889ecb43d2aa3ff66a07486380
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178131B2

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