Potassium Hydroxide → 2-Propyl-1H-pyrrolo[2,3-b]pyridine

HRID 893376Notes

Reaction equation

HRID 893376 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[CH2:19][CH2:20][CH3:21])(=O)=O)C=CC=CC=1.[OH-].[K+]>CO>[CH2:19]([C:11]1[NH:10][C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[CH:12]=1)[CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 198922051-(Phenylsulfonyl)-2-propyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 189467102-Propyl-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(benzenesulfonyl)-2-propyl-1H-pyrrolo[2,3-b]pyridine (67 mg) and KOH (200 mg) in MeOH (30 mL) was heated to reflux for 3 h. The mixture was concentrated, neutralized by addition of 1N HCl, extracted (EtOAc) and purified (SiO2, 25% EtOAc/hexane) to give 2-propyl-1H-pyrrolo-[2,3-b]pyridine as a solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. concentrationThe mixture was concentrated
  4. additionneutralized by addition of 1N HCl
  5. extractionextracted (EtOAc)
  6. custompurified (SiO2, 25% EtOAc/hexane)

Sources & evidence

ORD record
ord-98d7a0621934468da4aa39e8bb3eb98e
Source dataset
uspto-grants-1992_06
Patent number
US05124335

Reaction notes

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