Hydrogen Bromide → HCID 67398950, compound

HRID 70696Notes

Reaction equation

HRID 70696 reaction equation
Br.[Cl:2][C:3]1[CH:4]=[C:5]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([O:20]C)[N:14]=2)=[O:12])[CH:6]=[CH:7][C:8]=1[S:9][CH3:10].C(=O)(O)[O-].[Na+]>C(#N)C>[Cl:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[S:9][CH3:10])[C:11]([C:13]1[NH:14][C:15](=[O:20])[C:16]([CH3:19])=[CH:17][CH:18]=1)=[O:12]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 58452270HCID 58452270, compound

Product 1

HCID 67398950HCID 67398950, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
95 °C

Procedure

48% hydrobromic acid (7 mL) was added to a solution of [3-chloro-4-(methylsulfanyl)phenyl](6-methoxy-5-methylpyridin-2-yl)methanone obtained in Reference Example 1-40 (700 mg) in acetonitrile (7 mL) at room temperature, and the mixture was stirred at 95° C. for one hour. The reaction solution was neutralized with saturated aqueous sodium bicarbonate at room temperature and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=50:1) to give 6-[3-chloro-4-(methylsulfanyl)benzoyl]-3-methylpyridin-2(1H)-one as a pale yellow solid (632 mg, 95%).

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was then evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-ff7743f1fcb844c0a563e84e3e45ae65
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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