Hydrogen Bromide → HCID 58452433, compound

HRID 70539Notes

Reaction equation

HRID 70539 reaction equation
Br.[Br:2]/[C:3](/[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18]C)[N:12]=1)=[CH:4]\[C@@H:5]1[NH:9][C:8](=[O:10])[CH2:7][CH2:6]1.O>O1CCOCC1>[Br:2]/[C:3](/[C:11]1[NH:12][C:13](=[O:18])[C:14]([Cl:17])=[CH:15][CH:16]=1)=[CH:4]\[C@H:5]1[CH2:6][CH2:7][C:8](=[O:10])[NH:9]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 58452317(5R)-5-[(Z)-2-bromo-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one

Product 1

HCID 58452433HCID 58452433, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

48% hydrobromic acid (2 mL) was added to a solution of (5R)-5-[(Z)-2-bromo-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one (115 mg) in 1,4-dioxane (3 mL), and the mixture was stirred at 65° C. for one hour. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=10:0→4:1) to give the title compound as a colorless powder (40 mg, 37%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=10:0→4:1)

Sources & evidence

ORD record
ord-d463d54529ec456088cf0930fbb68622
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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