Potassium Hydroxide → 1H-Pyrrolo(2,3-b)pyridine-2-carbaldehyde

HRID 2274995Notes

Reaction equation

HRID 2274995 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[CH:19]=[O:20])(=O)=O)C=CC=CC=1.[OH-].[K+]>CO.O>[NH:10]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[CH:12]=[C:11]1[CH:19]=[O:20]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 566921991-(Phenylsulfonyl)-1H-pyrrolo(2,3-b)pyridine-2-carboxaldehyde

Product 1

HCID 218736801H-Pyrrolo(2,3-b)pyridine-2-carbaldehydeYield 78.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde (2.5 g, 8.73 mmol) in methanol (50 mL) stirred under nitrogen at r.t. was added a solution of KOH (1.96 g, 34.9 mmol) in water (5 mL) dropwise during 1 min. The reaction mixture was stirred at r.t. for 30 min, TLC showed complete conversion. The reaction mixture was diluted with H2O (150 mL), extracted with dichloromethane (3×150 mL) and the organic phase was washed with saturated brine (3×50 mL), water 100 mL, dried over sodium sulfate and evaporated in vacuo to give the title compound as a yellow solid (1 g, 54.9% yield) which was used in the next reaction without further purification.

Workup

  1. extractionextracted with dichloromethane (3×150 mL)
  2. washthe organic phase was washed with saturated brine (3×50 mL), water 100 mL
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-5a1a346babc7480ba5a7fa4b88ccb193
Source dataset
uspto-grants-2015_09
Patent number
US09127003B2

Reaction notes

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