Cesium fluoride → Methyl 5-bromo-2-fluoropyridine-3-carboxylate

HRID 1986093Notes

Reaction equation

HRID 1986093 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[F-:13].[Cs+]>CS(C)=O.O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([F:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 25953Cesium fluorideHCID 2763343Methyl 5-bromo-2-chloronicotinate

Product 1

HCID 45588056Methyl 5-bromo-2-fluoropyridine-3-carboxylateYield 57%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 5-bromo-2-chloronicotinate (170 mg, 0.68 mmol) in 3 mL of DMSO was added CsF (152 mg, 1.0 mmol). The solution was stirred at room temperature for 2 d and then heated at 60° C. for 4 h. After cooling, the mixture was diluted with 30 mL of H2O. The aqueous solution was extracted with EtOAc and the combined organic layers were washed with brine, and dried over MgSO4. After filtration and concentration in vacuo, the residue was purified by silica gel flash chromatography to give the desired product (90 mg, 57% yield). MS (ESI+) m/z 234.06, 236.09 (M+H)+.

Workup

  1. temperatureheated at 60° C. for 4 h
  2. temperatureAfter cooling
  3. extractionThe aqueous solution was extracted with EtOAc
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration and concentration in vacuo
  7. customthe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-fb0ccce1bc1a4da6869dc440824044df
Source dataset
uspto-grants-2009_06
Patent number
US07547782B2

Reaction notes

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