1H-Pyrrolo(2,3-b)pyridine → HCID 178526243, compound

HRID 269493Notes

Reaction equation

HRID 269493 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.C1C=C(Cl)C=C(C(OO)=[O:18])C=1>COCCOC>[NH:1]1[C:9]2=[N+:8]([O-:18])[CH:7]=[CH:6][CH:5]=[C:4]2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 178526243HCID 178526243, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 7-azaindole (2.0 g, 16.93 mmol) in dry DME (60 mL) was added m-CPBA (70%) (6.3 g, 25.55 mmol). The resulting yellow solution was stirred at RT for 2 h during which time the product was precipitated out. The mixture was cooled and the light yellow product was isolated by filtration and washed with ether. A suspension of this yellow solid in water (60 mL) was basified to pH 9 with sat. K2CO3 solution. The solution was then cooled in refrigerator for a weekend. A white precipitate was collected by filtration and the filtrate was half evaporated and cooled again to repeat the crystallization procedure. The precipitates were combined and dried on the pump for the next reaction (1.5 g, 11.2 mmol, 66%). MS (ES+): m/e=135.1 (M+H); LC: 1.37 min.

Workup

  1. customwas precipitated out
  2. temperatureThe mixture was cooled
  3. customthe light yellow product was isolated by filtration
  4. washwashed with ether
  5. additionA suspension of this yellow solid in water (60 mL)
  6. temperatureThe solution was then cooled in refrigerator for a weekend
  7. filtrationA white precipitate was collected by filtration
  8. customevaporated
  9. temperaturecooled again
  10. customthe crystallization procedure
  11. customdried on the pump for the next reaction (1.5 g, 11.2 mmol, 66%)
  12. custom1.37 min.

Sources & evidence

ORD record
ord-29d8bb7a6ded4e5aa6b4e6374e11e9fc
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

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