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

HRID 16423Notes

Reaction equation

HRID 16423 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:28][S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[N:15]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:16]=[CH:17][C:10]=12>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([NH:28][S:29]([C:32]2[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=2)(=[O:30])=[O:31])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[N:15]([S:18]([C:21]3[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=3)(=[O:20])=[O:19])[CH2:16][CH2:17][C:10]=12

Participants

4

Reactant 1

HCID 17979281N-[3-Fluoro-4-({1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)phenyl]-4-methylphenylsulfonamide

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

50 mg (0.09 mmol) of N-[3-fluoro-4-({1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)phenyl]-4-methylphenylsulfonamide (from example XLIV) are dissolved in 30 ml of methanol, and 48.2 mg (0.05 mmol) of 10% palladium on activated carbon are added. The mixture is hydrogenated overnight under a hydrogen pressure of 3.5 bar. The palladium is then filtered off with suction through kieselguhr and washed with ethanol, and the filtrate is concentrated.

Workup

  1. filtrationThe palladium is then filtered off with suction through kieselguhr
  2. washwashed with ethanol
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-3f2cd3a689cc460385aac995c689043b
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

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