Sodium Hydroxide → [4-(2,3-Dihydro-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenyl]amine

HRID 16424Notes

Reaction equation

HRID 16424 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:28]S(C2C=CC(C)=CC=2)(=O)=O)[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)[CH2:16][CH2:17][C:10]=12.[OH-].[Na+]>S(=O)(=O)(O)O>[NH:15]1[C:11]2=[N:12][CH:13]=[CH:14][C:9]([O:8][C:7]3[CH:6]=[CH:5][C:4]([NH2:28])=[CH:3][C:2]=3[F:1])=[C:10]2[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 17979343N-[3-Fluoro-4-({1-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)phenyl]-4-methylphenylsulfonamide

Product 1

HCID 17979279[4-(2,3-Dihydro-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenyl]amine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

50 mg (0.09 mmol) of N-[3-fluoro-4-({1-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)phenyl]-4-methylphenylsulfonamide (from example XLV) are dissolved in 1.00 ml of sulfuric acid (95%) and stirred at RT overnight. With ice-cooling, the reaction solution is neutralized with 20% strength aqueous sodium hydroxide solution, and the mixture is extracted three times with ethyl acetate. The organic phase is dried over anhydrous magnesium sulfate and concentrated.

Workup

  1. temperatureWith ice-cooling
  2. extractionthe mixture is extracted three times with ethyl acetate
  3. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9eeb96bce8014f918399044faa5821c6
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

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