Hydrogen Bromide → HCID 67399727, compound

HRID 70708Notes

Reaction equation

HRID 70708 reaction equation
Br.[CH:2]1([S:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[C:16]([O:24]C)[N:15]=3)=[O:13])=[CH:8][CH:7]=2)[CH2:4][CH2:3]1.O>O1CCOCC1>[CH:2]1([S:5][C:6]2[CH:7]=[CH:8][C:9]([C:12]([C:14]3[NH:15][C:16](=[O:24])[C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=3)=[O:13])=[CH:10][CH:11]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 58452661HCID 58452661, compound

Product 1

HCID 67399727HCID 67399727, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

48% hydrobromic acid (2 mL) was added to a solution of [4-(cyclopropylsulfanyl)phenyl][6-methoxy-5-(trifluoromethyl)pyridin-2-yl]methanone obtained in Reference Example 1-68 (400 mg) in 1,4-dioxane (4 mL), and the mixture was stirred at 65° C. for one hour. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→1:5) to give 6-{[4-(cyclopropylsulfanyl)phenyl]carbonyl}-3-(trifluoromethyl)pyridin-2(1H)-one (210 mg, 55%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customafter which the solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→1:5)

Sources & evidence

ORD record
ord-07d6a2cdde0b459fabe3aa3c515e4a1d
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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