Ammonium formate → HCID 178419834, compound

HRID 2204645Notes

Reaction equation

HRID 2204645 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[C:18]3=[C:19]4[CH:25]=[CH:24][NH:23][C:20]4=[N:21][CH:22]=[C:17]3[NH:16][N:15]=2)[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[OH-].[OH-].[Pd+2].CCO>[NH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[C:18]3=[C:19]4[CH:25]=[CH:24][NH:23][C:20]4=[N:21][CH:22]=[C:17]3[NH:16][N:15]=2)[CH2:9]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 178420310HCID 178420310, compound

Product 1

HCID 178419834HCID 178419834, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(1-benzylpiperidin-3-yl)-3,6-dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridine (0.18 g, 0.54 mmol), Pearlman's catalyst (0.05 g, 0.36 mmol) and ammonium formate (0.684 g, 10.8 mmol) was heated in EtOH (20 mL) at reflux for about 1 h. The catalyst was removed by filtration through a Celite® pad and the filtrate concentrated in vacuo to yield 1-(piperidin-3-yl)-3,6-dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridine (0.13 g, 0.543 mmol, quantitative) as a yellow amorphous solid that was used directly in the next step without further purification: LC/MS (Table 2, Method a) Rt=1.31 min; MS m/z: 242 (M+H)+.

Workup

  1. temperatureat reflux for about 1 h
  2. customThe catalyst was removed by filtration through a Celite® pad
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-092b636fec5f4ff095c5c4cb90f650de
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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