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Sodium Hydroxide → 3-fluoro-4-[(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]aniline

HRID 2192162
Notes
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Reaction equation

HRID 2192162 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:29]C(=O)C)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[N:15](S(C3C=CC(C)=CC=3)(=O)=O)[CH:16]=[C:17]([CH3:18])[C:10]=12.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[NH:15][CH:16]=[C:17]([CH3:18])[C:10]=12)[NH2:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59741018N-[3-Fluoro-4-({3-methyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)phenyl]acetamide

Product 1

HCID 179793083-fluoro-4-[(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

267 mg (0.59 mmol) of N-[3-fluoro-4-({3-methyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]-pyridin-4-yl}oxy)phenyl]acetamide are dissolved in 10 ml of ethanol. 5 ml of 20% strength aqueous sodium hydroxide solution are added, and the reaction mixture is heated at 90° C. overnight. Most of the solvent is removed under reduced pressure. The residue is taken up in ethyl acetate and shaken with sodium carbonate solution. The organic phase is washed with sodium chloride solution and dried over magnesium sulfate, and the solvent is removed under reduced pressure.

Workup

  1. customMost of the solvent is removed under reduced pressure
  2. washThe organic phase is washed with sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-b5c02ffbf2064786b65f31b1032437f1
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08329716B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes