1H-Pyrrolo(2,3-b)pyridine → 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid ethyl ester

HRID 1437181Notes

Reaction equation

HRID 1437181 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[CH2:10]([O:12][C:13]([N:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1)=[O:14])[CH3:11].[OH-].[K+]>CO>[CH2:10]([O:12][C:13]([N:15]1[CH2:16][CH:17]=[C:18]([C:3]2[C:4]3[C:9](=[N:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH2:19][CH2:20]1)=[O:14])[CH3:11]

Participants

5

Reactant 3

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14797Potassium HydroxideHCID 34767Ethyl 4-oxo-1-piperidinecarboxylate

Product 1

HCID 457902484-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid ethyl esterYield 57.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension 5.51 g (0.05 mol) of 7-azaindol, 9.6 g (0.056 mol) of 4-oxo-piperidine-1-carboxylic acid ethyl ester and 5 g (0.075 mol) of potassium hydroxide in 120 ml of methanol was heated at 75° C. for 16 hours. The crude mixture was cooled at room temperature and the precipitate formed was filtered off. 7.8 g (57% of yield) of 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid ethyl ester were obtained.

Workup

  1. customthe precipitate formed
  2. filtrationwas filtered off

Sources & evidence

ORD record
ord-f42061fbdbf741f083d003122df06c54
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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