Ammonium formate → tert-butyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate

HRID 1675030Notes

Reaction equation

HRID 1675030 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH:11]=2)=[CH:2]1.C([O-])=O.[NH4+]>[Pd].C(O)C>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:2]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 45790246Tert-butyl 4-(1H-pyrrolo[2,3-B]pyridin-3-YL)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 49758876tert-butyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylateYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

tert-Butyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.35 g, 4.51 mmol), ammonium formate (1.42 g, 22.55 mmol) and 5% palladium on activated carbon (50 mg) in ethanol (25 mL) were stirred and refluxed for 1 hour. The resulting mixture was cooled to room temperature and filtered through diatomaceous earth. The filtrate was concentrated by evaporation then treated with dilute aqueous ammonium chloride (50 mL) and extracted with DCM. The extract was washed with water, dried over MgSO4 and evaporated to a colourless solid. The solid was triturated with ether then collected by filtration and dried under vacuum to give tert-butyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate (1.088 g, 80%) as a colourless solid.

Workup

  1. temperaturerefluxed for 1 hour
  2. filtrationfiltered through diatomaceous earth
  3. concentrationThe filtrate was concentrated by evaporation
  4. additionthen treated with dilute aqueous ammonium chloride (50 mL)
  5. extractionextracted with DCM
  6. washThe extract was washed with water
  7. dry with materialdried over MgSO4
  8. customevaporated to a colourless solid
  9. customThe solid was triturated with ether
  10. filtrationthen collected by filtration
  11. customdried under vacuum

Sources & evidence

ORD record
ord-40f3ab191ab045c1b9dcb6f3eef867b2
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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