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

HRID 2192164Notes

Reaction equation

HRID 2192164 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][C:11]=2[O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20]C(=O)C(F)(F)F)=[CH:16][C:15]=2[F:27])[NH:6][CH:5]=1>O1CCCC1>[Cl:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][C:11]=2[O:13][C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:15]=2[F:27])[NH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59741002N-{4-[(3-Chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluorophenyl}-2,2,2-trifluoroacetamide

Product 1

HCID 597410163-fluoro-4-[(3-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]aniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8 ml of 1N aqueous sodium hydroxide solution are added to a solution of 637 mg (1.70 mmol) of N-{4-[(3-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluorophenyl}-2,2,2-trifluoroacetamide in tetrahydrofuran (10 ml). The reaction is stirred overnight. The solution is extracted with ethyl acetate (two times 20 ml). The combined organic phases are washed with a saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated. This gives a solid which is not purified any further.

Workup

  1. extractionThe solution is extracted with ethyl acetate (two times 20 ml)
  2. washThe combined organic phases are washed with a saturated sodium chloride solution
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThis gives a solid which
  6. customis not purified any further

Sources & evidence

ORD record
ord-3ea840c1757e47f5a6a834d4a3772fca
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

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