4-methyl-5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine → 4-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-amine

HRID 576683Notes

Reaction equation

HRID 576683 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][N:5]=[C:4]2[N:11]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:12]=[CH:13][C:3]=12.[H][H]>C1COCC1.CCO.[Pd]>[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][N:5]=[C:4]2[N:11]([S:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)(=[O:16])=[O:15])[CH:12]=[CH:13][C:3]=12

Participants

6

Reactant 2

HCID 671156174-methyl-5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 671156214-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-amineYield 99.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-methyl-5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine, (410 mg, 1.29 mmol) in THF (15 mL) and EtOH (10 mL) was added 10% palladium on carbon (10 wt % of Pd/C; 45 mg) under argon. The mixture was hydrogenated using a hydrogen balloon at room temperature for 16 hours. The reaction mixture was flushed with nitrogen and filtered through a plug of Celite® and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel using hexane:EtOAc (4:6) to get 4-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-amine, (370 mg). 1H NMR (300 MHz, CD3OD) δ: 7.96-8.04 (m, 2H), 7.83 (s, 1H), 7.53-7.64 (m, 2H), 7.42-7.52 (m, 2H), 6.65 (d, J=4.1 Hz, 1H), 2.26 (s, 3H).

Workup

  1. customat room temperature
  2. customfor 16 hours
  3. customThe reaction mixture was flushed with nitrogen
  4. filtrationfiltered through a plug of Celite®
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-b529fff1fc964056a5456528f6d2c056
Source dataset
uspto-grants-2015_05
Patent number
US09040532B2

Reaction notes

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