Potassium Carbonate → HCID 86700243, compound

HRID 879436Notes

Reaction equation

HRID 879436 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](F)[CH:3]=1.Cl.[F:10][C:11]([F:22])([F:21])[C:12]1[N:16]2[CH2:17][CH2:18][NH:19][CH2:20][C:15]2=[N:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:19]2[CH2:18][CH2:17][N:16]3[C:12]([C:11]([F:22])([F:10])[F:21])=[N:13][N:14]=[C:15]3[CH2:20]2)[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27628514-Bromo-2-fluoropyridineHCID 119613713-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

Product 1

HCID 86700243HCID 86700243, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromo-2-fluoropyridine (0.216 mL, 2.1 mmol), 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride (0.399 g, 1.75 mmol) and potassium carbonate (0.482 g, 3.49 mmol) in anhydrous DMF (7.0 mL) was heated at 100° C. for 16 h. Reaction mixture was cooled, diluted with ethyl acetate, washed with 5% lithium chloride solution (2×), brine, dried (MgSO4), filtered, concentrated and purified by CombiFlash (0 to 50% EtOAc/Hex) to give product. LCMS-ESI+: calc'd for C11H10BrF3N5: 348.0. (M+H+); Found: 348.2 (M+H+).

Workup

  1. customReaction mixture
  2. temperaturewas cooled
  3. washwashed with 5% lithium chloride solution (2×), brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by CombiFlash (0 to 50% EtOAc/Hex)
  8. customto give product

Sources & evidence

ORD record
ord-607d68b1572e42cfbc7c52a7537c6515
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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