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

HRID 408207

Reaction equation

HRID 408207 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 60205349N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluorobenzamideYield 78.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d71dba44536d4f12820c4eef8ea1a259
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Linked notes

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