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

HRID 1437182Notes

Reaction equation

HRID 1437182 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH:10]=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

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

Product 1

HCID 49759051Ethyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylateYield 62.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7.8 g (0.029 mol) of 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid ethyl ester were dissolved in 250 ml of ethanol and 7.8 g of palladium over carbon at 10% were added. The crude mixture was hydrogenated at 30 psi for 24 hours. After filtering the catalyst and removal of the solvent at reduced pressure, 4.95 g (62% of yield) of 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-piperidine-1-carboxylic acid ethyl ester were obtained.

Workup

  1. filtrationAfter filtering
  2. customthe catalyst and removal of the solvent at reduced pressure

Sources & evidence

ORD record
ord-82bcefd53bd944f386fc1bc90628df60
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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