Acetonitrile → HCID 86703140, compound

HRID 2410123Notes

Reaction equation

HRID 2410123 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][N:5]=[C:4](Cl)[CH:3]=1.S([O:16][CH3:17])(OC)(=O)=O.C(#N)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][N:5]([CH3:4])[C:17](=[O:16])[CH:3]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 467387064-Bromo-2-chloro-5-methoxypyridine

Product 1

HCID 86703140HCID 86703140, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromo-2-chloro-5-methoxypyridine (1 g, 4.5 mmol) in dimethyl sulfate (1.9 mL, 19.5 mmol) was stirred at 120° C. for 16 h in a sealed tube. After cooling, acetonitrile and a saturated aqueous NaHCO3 solution were added and the mixture was stirred at rt over week-end. DCM was added and extracted. The organic layer was dried (Na2SO4), filtered and concentrated to give the title compound. tR: 0.57 min (LC-MS 2); ESI-MS: 218.0/220.0 [M+H]+ (LC-MS 2).

Workup

  1. temperatureAfter cooling
  2. extractionextracted
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-485e28b23245410b82806ecaab39fd7e
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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