Sodium Hydroxide → (3-amino-2,6-difluoro-phenyl)-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

HRID 217588Notes

Reaction equation

HRID 217588 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([C:18]([C:20]2[C:28]3[C:23](=[N:24][CH:25]=[C:26]([Cl:29])[CH:27]=3)[NH:22][CH:21]=2)=[O:19])[C:12]=1[F:30])C1C=CC=CC=1.[OH-].[Na+]>O>[NH2:10][C:11]1[C:12]([F:30])=[C:13]([C:18]([C:20]2[C:28]3[C:23](=[N:24][CH:25]=[C:26]([Cl:29])[CH:27]=3)[NH:22][CH:21]=2)=[O:19])[C:14]([F:17])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58087931[3-(5-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl]-carbamic acid benzyl ester

Product 1

HCID 58086398(3-amino-2,6-difluoro-phenyl)-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanoneYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[3-(5-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]-carbamic acid benzyl ester (7, 800 mg, 1.81 mmol) was added to 15.00 mL of 10 M sodium hydroxide and warmed to reflux overnight. The reaction mixture was diluted with 30 mL of water and extracted with ethyl acetate. The organic layer was separated, dried, filtered and the filtrate concentrated under vacuum to give the desired compound (8, 450 mg, 81%).

Workup

  1. temperaturewarmed
  2. temperatureto reflux overnight
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-a5fa6147cc2b497aad0ed5addd1d5050
Source dataset
uspto-grants-2012_06
Patent number
US08198273B2

Reaction notes

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