Hydrochloric Acid → Hydrochloric Acid

HRID 75314Notes

Reaction equation

HRID 75314 reaction equation
[ClH:1].O1CCOCC1.[Br:8][C:9]1[CH:10]=[C:11]2[N:27]([CH3:28])[CH:26]=[CH:25][C:12]2=[N:13][C:14]=1[C@H:15]([NH:17]C(=O)OC(C)(C)C)[CH3:16]>>[ClH:1].[Br:8][C:9]1[CH:10]=[C:11]2[N:27]([CH3:28])[CH:26]=[CH:25][C:12]2=[N:13][C:14]=1[C@H:15]([NH2:17])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86708015(R)-tert-butyl (1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate

Product 2

HCID 313Hydrochloric AcidHCID 86708014(R)-1-(6-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethan-1-amine

Procedure

A 100 mL pear flask was charged with 4.0M hydrogen chloride in dioxane (2.117 mL, 8.47 mmol) and cooled in an ice-bath. To the beige solution was added (R)-tert-butyl (1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate (3 g, 8.47 mmol) in one portion. The ice-bath was removed and the mixture was stirred at RT for 90 minutes. Ethoxyethane was added (80 mL) and the mixture was cooled in an ice-bath. A resulting white precipitate was collected on a fritted glass funnel to give an HCl salt of the title compound, which was used without further purification.

Workup

  1. temperaturecooled in an ice-bath
  2. customThe ice-bath was removed
  3. additionEthoxyethane was added (80 mL)
  4. temperaturethe mixture was cooled in an ice-bath
  5. customA resulting white precipitate was collected on a fritted glass funnel

Sources & evidence

ORD record
ord-89b6c08ca0f744f696cb6a337bdaae24
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Reaction notes

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