Hydrogen Peroxide → 2-(5-Methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4 Carboxamide

HRID 549028Notes

Reaction equation

HRID 549028 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12]1[N:22](S(C2C=CC(C)=CC=2)(=O)=O)[C:15]2[N:16]=[CH:17][CH:18]=[C:19]([C:20]#[N:21])[C:14]=2[CH:13]=1.[OH-:33].[Na+].OO>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12]1[NH:22][C:15]2[N:16]=[CH:17][CH:18]=[C:19]([C:20]([NH2:21])=[O:33])[C:14]=2[CH:13]=1

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 14798Sodium HydroxideHCID 224772152-(5-methoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile

Product 1

HCID 224772732-(5-Methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4 Carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 2-(5-methoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-4 carbonitrile [0.25 g, Reference Example 67(e)] in methanol (25 mL) was treated with sodium hydroxide solution (1.5 g in 4 mL water). The mixture was cooled in an ice-bath and then treated dropwise with hydrogen peroxide (0.35 mL, 30%). After stirring at room temperature for 1 hour a further aliquot of hydrogen peroxide (0.3 mL) was added to the reaction mixture and stirring was continued for a further 3 hours then the reaction was quenched by addition of sodium metabisulfite to remove excess hydrogen peroxide. The reaction mixture was then diluted with water (75 mL) and extracted twice with ethyl acetate (50 mL). The combined extracts were washed twice with brine (30 mL), then dried over sodium sulfate and then evaporated. The residual yellow solid was subjected to chromatography on silica eluting with a mixture of ethyl acetate and dichloromethane (1:1, v/v) to give, after trituration with methanol and washing with diethyl ether, the title compound (50 mg) as a yellow solid, m.p.>320° C. MS: 307 (MH+).

Workup

  1. temperatureThe mixture was cooled in an ice-bath
  2. additionwas added to the reaction mixture
  3. customthe reaction was quenched by addition of sodium metabisulfite
  4. customto remove excess hydrogen peroxide
  5. additionThe reaction mixture was then diluted with water (75 mL)
  6. extractionextracted twice with ethyl acetate (50 mL)
  7. washThe combined extracts were washed twice with brine (30 mL)
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. additionThe residual yellow solid was subjected to chromatography on silica eluting with a mixture of ethyl acetate and dichloromethane (1:1
  11. customv/v) to give
  12. washafter trituration with methanol and washing with diethyl ether

Sources & evidence

ORD record
ord-1982367f27df4df498286651c2236545
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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