Methanol → 5-Nitro-7-azaindole

HRID 2222582Notes

Reaction equation

HRID 2222582 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[CH:12]=[CH:11][N:10](S(C3C=CC=CC=3)(=O)=O)[C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2].CO.[OH-].[Na+]>ClCCl>[N+:1]([C:4]1[CH:5]=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 497589095-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 115211405-Nitro-7-azaindoleYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (10.2 g, 33 mmol) in methanol (250 mL) powdered sodium hydroxide (2 g, 50 mmol) was added. After stirring at room temperature for 30′ more powdered sodium hydroxide (2 g, 50 mmol) and dichloromethane (50 mL) were added and stirring was prolonged for additional 30′. After concentration, a solution of 2N HCl (50 mL) and water (200 mL) was added and the obtained mixture was filtered. The yellow cake was washed with water and dried to give 5-nitro-1H-pyrrolo[2,3-b]pyridine (4.6 g, 28.2 mmol, 85% yield).

Workup

  1. additionwas added
  2. additionwere added
  3. concentrationAfter concentration
  4. additiona solution of 2N HCl (50 mL) and water (200 mL) was added
  5. filtrationthe obtained mixture was filtered
  6. washThe yellow cake was washed with water
  7. customdried

Sources & evidence

ORD record
ord-a737748ba2e84dc2ac10568f9b7c1205
Source dataset
uspto-grants-2008_05
Patent number
US07371862B2

Reaction notes

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