5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine → 1-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-amine

HRID 1515848Notes

Reaction equation

HRID 1515848 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:19]([O-])=O)[CH:18]=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O1CCCC1.[Pd]>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([NH2:19])[CH:18]=[C:13]3[CH:12]=[CH:11]2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 497589095-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 672291641-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-amineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridine (2.8 g, 9.24 mmol) in tetrahydrofuran (50 mL) was added 10% palladium on activated carbon (0.98 g). The resulting mixture was stirred under hydrogen (50 psi) for 48 h at room temperature. The catalyst was removed by filtration and the filtrate was concentrated to afford 1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-5-ylamine (2.52 g, 100%) as a yellow oil which was used in the next step without purification: LC/MS m/e calcd for C13H11N3O2S [M+H]+ 274.32, observed 274.1.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-fb3fb45e7ec14b96bccb1431028ecdfb
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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