Sodium Hydroxide → 2-[4-(4-Amino-2-fluorophenoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]ethanol
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:31]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]([CH2:18][CH2:19][OH:20])[C:10]=12.[OH-].[Na+]>C(O)C>[NH2:31][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[NH:15][CH:16]=[C:17]([CH2:18][CH2:19][OH:20])[C:10]=23)=[C:2]([F:1])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
470 mg (0.97 mmol) of N-[3-fluoro-4-({3-(2-hydroxyethyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo-[2,3-b]pyridin-4-yl}oxy)phenyl]acetamide are dissolved in 25 ml of ethanol. 10 ml of 20% strength aqueous sodium hydroxide solution are added, and the reaction mixture is stirred at 90° C. overnight. Most of the solvent is removed under reduced pressure, the residue is taken up in ethyl acetate and partitioned between ethyl acetate and 1N aqueous sodium hydroxide solution and extracted. The organic phase is washed with 1N aqueous sodium hydroxide solution and dried over magnesium sulfate, and the solvent is removed under reduced pressure.
Workup
- customMost of the solvent is removed under reduced pressure
- custompartitioned between ethyl acetate and 1N aqueous sodium hydroxide solution
- extractionextracted
- washThe organic phase is washed with 1N aqueous sodium hydroxide solution
- dry with materialdried over magnesium sulfate
- customthe solvent is removed under reduced pressure
Sources & evidence
- ORD record
- ord-67fd7d440ff94acb829dae79630d4397
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329716B2
Reaction notes
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