Boron tribromide → HCID 68676614, compound

HRID 2233020Notes

Reaction equation

HRID 2233020 reaction equation
C([N:5]1[C:21](=[O:22])[N:8]2[CH:9]=[C:10]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:11]=[C:12](Cl)[C:7]2=[N:6]1)(C)(C)C.B(Br)(Br)[Br:24]>ClCCCl>[Br:24][C:12]1[C:7]2[N:8]([C:21](=[O:22])[NH:5][N:6]=2)[CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[N:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68675948HCID 68675948, compound

Product 1

HCID 68676614HCID 68676614, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
125 °C

Procedure

A solution of 335 mg of 2-tert-butyl-8-chloro-6-(4-chloro-phenyl)-2H-[1,2,4]triazolo[4,3-a]pyrazin-3-one in 1,2-dichloroethane (10.0 mL) was treated with 2.35 g of boron tribromide and the solution was heated to 125° C. in a sealed tube. After two h, the reaction was cooled to ambient temperature and the excess boron reagent was carefully destroyed by the careful addition of water. The reaction mixture was basified with 2N NaOH to pH 9 and then acidified with sat. ammonium chloride solution. The aqueous layer was extracted with EtOAc and the organic layers were washed with sat. sodium chloride solution, dried over sodium sulfate, filtered, and concentrated to provide 8-bromo-6-(4-chloro-phenyl)-2H-[1,2,4]triazolo[4,3-a]pyrazin-3-one as a tan solid. MS (M+H+)=438.3.

Workup

  1. temperatureAfter two h, the reaction was cooled to ambient temperature
  2. customthe excess boron reagent was carefully destroyed by the careful addition of water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe organic layers were washed with sat. sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-af5273247e1146c78eee2f8b91d89ea5
Source dataset
uspto-grants-2010_05
Patent number
US07709473B2

Reaction notes

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