Potassium Carbonate → 7-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-methyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

HRID 1889066

Reaction equation

HRID 1889066 reaction equation
Br[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[C:14]=3[Cl:23])=[O:12])[CH2:10][C:5]2=[N:4][N:3]=1.[CH3:24]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:23][C:14]1[C:15]([C:19]([F:22])([F:21])[F:20])=[CH:16][CH:17]=[CH:18][C:13]=1[C:11]([N:9]1[CH2:8][CH2:7][N:6]2[C:2]([CH3:24])=[N:3][N:4]=[C:5]2[CH2:10]1)=[O:12]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 665992213-Bromo-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

Product 1

HCID 665992867-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-methyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

3-Bromo-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (150 mg, 0.366 mmol, e.g. see Example 1 for methods of preparation) was dissolved in 1,4-dioxane (3 mL) and treated with trimethylboroxine (55.2 mg, 0.439 mmol, commercially available e.g. from Sigma-Aldrich or Thermo Fischer Scientific), potassium carbonate (76 mg, 0.549 mmol) and tetrakis(triphenylphosphine)palladium(0) (42.3 mg, 0.037 mmol). The reaction mixture, under argon, was heated at 110° C. for 20 hours. The mixture was then cooled, diluted with water and extracted with ethyl acetate (three times). The organic phase was dried and evaporated. The residue was purified on the mass-directed automated (preparative) HPLC (MDAP) and the residue was triturated with isohexane to give 7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-methyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (0.028 g) as a white solid.

Workup

  1. temperatureThe mixture was then cooled
  2. extractionextracted with ethyl acetate (three times)
  3. customThe organic phase was dried
  4. customevaporated
  5. customThe residue was purified on the
  6. customthe residue was triturated with isohexane

Sources & evidence

ORD record
ord-21ad6dd963fb4c0a9440a660e6ad339d
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Linked notes

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