Potassium Bromide → HCID 22050873, compound

HRID 1866964Notes

Reaction equation

HRID 1866964 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[C:9](=[O:21])[C:8]=1[Br:22])(=O)=O.[K+].[Br-:26]>CN(C)C(=O)C>[Br:22][C:8]1[C:9](=[O:21])[N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[CH:11]=[CH:12][C:7]=1[Br:26]

Participants

4

Reactant 2

HCID 253877Potassium BromideHCID 58710194HCID 58710194, compound

Product 1

HCID 22050873HCID 22050873, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

3-bromo-1-(3-fluorobenzyl)-2-oxo-1,2-dihydropyridin-4-yl trifluoromethanesulfonate (2.00 g, 4.65 mmol), KBr (5.53 g, 46.49 mmol), and 18-Crown-6-(0.10 g, 0.38 mmol) were dissolved in N,N-dimethylacetamide (26 mL). The reaction mixture was then heated at reflux for 16 hours. The reaction was concentrated and the resulting residue was partition between water (50 mL) and ethyl acetate (3×50 mL). The combined organics were washed with H2O (2×30 mL), brine (50 mL), dried over MgSO4, concentrated, and subjected to chromatography (silica gel, ethyl acetate with 10% methanol/hexane) to afford a brown solid (0.850 g, 51%).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 16 hours
  3. concentrationThe reaction was concentrated
  4. customthe resulting residue was partition between water (50 mL) and ethyl acetate (3×50 mL)
  5. washThe combined organics were washed with H2O (2×30 mL), brine (50 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ab40202a244f416a9ee0a985152f3675
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

Loading…