Tetrahydrofuran → 2-(5-chloro-1H-pyrrolo(2,3-b)pyridin-3-yl)ethan-1-amine hydrochloride

HRID 1777585Notes

Reaction equation

HRID 1777585 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][CH2:12][NH2:13])=[C:9]([Si](CC)(CC)CC)[NH:8][C:5]2=[N:6][CH:7]=1.C1COCC1>[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][CH2:12][NH2:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 668320582-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanamine

Product 1

HCID 668320612-(5-chloro-1H-pyrrolo(2,3-b)pyridin-3-yl)ethan-1-amine hydrochlorideYield 177.5%

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

2-(5-Chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanamine (0.360 g; 1.16 mmol) was dissolved in a 1M solution of tetrabutylammonium fluoride in THF (4 mL; 4 mmol). The mixture was stirred overnight at room temperature and was concentrated under reduced pressure. The residue was dissolved in dichloromethane. A 2M solution of hydrogen chloride in diethylether was added and the formed precipitate was collected by filtration and dried under reduced pressure to give 0.239 g (89%) of 2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanamine hydrochloride as a beige solid.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane
  3. additionA 2M solution of hydrogen chloride in diethylether was added
  4. filtrationthe formed precipitate was collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-dd84ab5b4b594d9bb5fe785f3dba9dde
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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