Ammonium Hydroxide → 1H-pyrrolo(2,3-b)pyridin-5-amine

HRID 1853486Notes

Reaction equation

HRID 1853486 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[OH-].[NH4+:12]>CCOC(C)=O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[NH:8]1[C:5]2=[N:6][CH:7]=[C:2]([NH2:12])[CH:3]=[C:4]2[CH:10]=[CH:9]1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 117151871H-pyrrolo(2,3-b)pyridin-5-amineYield 63%

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-bromo-1H-pyrrolo[2,3-b]pyridine (6.0 g, 30.45 mmol) in ammonium hydroxide (120 mL) was treated with copper sulphate pentahydrate (1.50 g, 6.09 mmol, 0.2 eq) and heated in a sealed tube overnight. The reaction was diluted with EtOAc and the insoluble black solid was filtered off. The filtrate was extracted (EtOAc/Water) and the organic layer washed with saturated aqueous ammonium chloride, followed by water and brine. The organics were dried over magnesium sulphate, filtered and evaporated to dryness to give the product as a pale brown solid (2.57 g, 63%)

Workup

  1. temperatureheated in a sealed tube overnight
  2. filtrationthe insoluble black solid was filtered off
  3. extractionThe filtrate was extracted (EtOAc/Water)
  4. washthe organic layer washed with saturated aqueous ammonium chloride
  5. dry with materialThe organics were dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-24eca72f41cb44f39f198b9c6dfbccb7
Source dataset
uspto-grants-2015_02
Patent number
US08962642B2

Reaction notes

Loading…