Trifluoroacetic acid → 5-(Azetidin-3-yloxy)-2-bromo-pyridine trifluoro-acetic acid salt

HRID 2069726Notes

Reaction equation

HRID 2069726 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:14]=[N:15][C:16]([Br:19])=[CH:17][CH:18]=2)[CH2:9]1)=O)(C)(C)C.[C:20]([OH:26])([C:22]([F:25])([F:24])[F:23])=[O:21]>C(Cl)Cl>[F:23][C:22]([F:25])([F:24])[C:20]([OH:26])=[O:21].[NH:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[N:15][CH:14]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 594737911-Boc-3-((6-bromopyridin-3-YL)oxy)azetidine

Product 1

HCID 866450865-(Azetidin-3-yloxy)-2-bromo-pyridine trifluoro-acetic acid saltYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(6-Bromo-pyridin-3-yloxy)-azetidine-1-carboxylic acid tert-butyl ester (1.08 g, 3.28 mmol) in DCM (30 mL), add TFA (10 mL). Let the mixture be stirred at room temperature for 2 hrs. LC-MS and TLC show reaction was complete. So evaporate all the solvent and excessive TFA. The residue brown solid 5-(Azetidin-3-yloxy)-2-bromo-pyridine trifluoro-acetic acid salt (1.06 g, 95% yield) was used directly for next step.

Workup

  1. customreaction
  2. customSo evaporate all the solvent and excessive TFA

Sources & evidence

ORD record
ord-5007a2684d13409689a090c81942dc69
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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