Potassium Carbonate → HCID 86686227, compound

HRID 2171667Notes

Reaction equation

HRID 2171667 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[N:6][CH:7]=1.Cl.[CH3:10][O:11][CH:12]1[CH2:15][NH:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:14]2[CH2:15][CH:12]([O:11][CH3:10])[CH2:13]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27831685-Bromo-2-fluoropyridineHCID 222428583-Methoxyazetidine hydrochloride

Product 1

HCID 86686227HCID 86686227, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

5-Bromo-2-fluoropyridine (1.7 g) was mixed with N,N-dimethylacetamide (5 ml), and 3-methoxyazetidine hydrochloride (335 mg) and potassium carbonate (1.5 g) were added thereto, followed by stirring at 100° C. overnight. The reaction mixture was concentrated under reduced pressure, and CHCl3 and water were then added thereto. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain 5-bromo-2-(3-methoxyazetidin-1-yl)pyridine (581 mg).

Workup

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and CHCl3 and water
  3. additionwere then added
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-e7cc9c47295d4bc3a597ce15303b2e22
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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