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

HRID 925327Notes

Reaction equation

HRID 925327 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 ether was added and the formed precipitate 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 ether was added
  4. filtrationthe formed precipitate collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-c9ab1145d6f9476f8ef35d506fd376cc
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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