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 1437187Notes

Reaction equation

HRID 1437187 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.C1COCC1.[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

5

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 54%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.3 g (12 mmol) of 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid ethyl ester were dissolved in 15 ml of ethanol and 5 ml of THF. Over this solution, 3.3 g of Pd over carbon at 10% were added. The crude mixture was hydrogenated at 30 psi for 48 hours. The catalyst was filtered off and the solvent removed under reduced pressure affording 1.55 g (54%) of 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-piperidine-1-carboxylic acid ethyl ester.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4fe46aadc29a4ac487af513c5e7a70f0
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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