Water → HCID 66599228, compound

HRID 1889067Notes

Reaction equation

HRID 1889067 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][N:17]2[CH:20]=[N:21][N:22]=[C:16]2[CH2:15]1)=[O:13].Br[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][N:17]2[C:20]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[N:21][N:22]=[C:16]2[CH2:15]1)=[O:13]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 122863-BromopyridineHCID 66599251HCID 66599251, compound

Product 1

HCID 66599228HCID 66599228, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

7-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (0.160 g, 0.484 mmol, e.g. see Example 3 for method of preparation), 3-bromopyridine (0.084 g, 0.532 mmol, commercially available e.g. from Sigma-Aldrich or Ryan Scientific), palladium(II) acetate (0.011 g, 0.048 mmol) and cesium carbonate (0.159 g, 0.489 mmol) in anhydrous 1,4-dioxane (2.5 mL) were heated, under argon, at 90° C. for 18 hours. The mixture was cooled, water added and extracted with ethyl acetate (three times). The combined organic phases were washed with water (twice), dried and evaporated. The residue was purified on the mass-directed automated (preparative) HPLC (MDAP) to give 7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-(3-pyridinyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (0.015 g).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate (three times)
  3. washThe combined organic phases were washed with water (twice),
  4. customdried
  5. customevaporated
  6. customThe residue was purified on the

Sources & evidence

ORD record
ord-5635a50544f749e7ae077f09e4cdde7f
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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