Hydrogen Peroxide → N-[3-Fluoro-4-({3-(2-hydroxyethyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)phenyl]acetamide

HRID 2192170Notes

Reaction equation

HRID 2192170 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:30][C:31](=[O:33])[CH3:32])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[N:15]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:16]=[C:17]([CH:18]=[CH2:19])[C:10]=12.B.[OH-:35].[Na+].OO>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:30][C:31](=[O:33])[CH3:32])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[N:15]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:21])=[O:22])[CH:16]=[C:17]([CH2:18][CH2:19][OH:35])[C:10]=12

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798Sodium HydroxideHCID 59740998N-[3-Fluoro-4-({1-[(4-methylphenyl)sulfonyl]-3-vinyl-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)phenyl]acetamide

Product 1

HCID 59740986N-[3-Fluoro-4-({3-(2-hydroxyethyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At 0° C., 890 mg (1.91 mmol) of N-[3-fluoro-4-({1-[(4-methylphenyl)sulfonyl]-3-vinyl-1H-pyrrolo[2,3-b]-pyridin-4-yl}oxy)phenyl]acetamide are initially charged in 28 ml of THF. 7.65 ml (7.65 mmol) of a 1M solution of borane in THF are added dropwise, and the mixture is stirred at RT for one hour. 14 ml of 1N aqueous sodium hydroxide solution and 14 ml of 30% strength hydrogen peroxide solution are then added carefully to the reaction mixture. The mixture is heated at 60° C. for one hour. For work-up, the reaction solution is partitioned between ethyl acetate and sodium bicarbonate solution. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried over sodium sulfate. The solvent is removed under reduced pressure. The product is purified by chromatography-on silica gel (mobile phase: dichloromethane/acetone 20:1 to 6.5:1).

Workup

  1. temperatureThe mixture is heated at 60° C. for one hour
  2. customFor work-up, the reaction solution is partitioned between ethyl acetate and sodium bicarbonate solution
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customThe product is purified by chromatography-on silica gel (mobile phase: dichloromethane/acetone 20:1 to 6.5:1)

Sources & evidence

ORD record
ord-1f8650fd555e4ede8690ac50b016d1d2
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

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