Potassium Carbonate → HCID 71086736, compound

HRID 571881Notes

Reaction equation

HRID 571881 reaction equation
I[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[N:3]=1.[NH:12]1[CH:16]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:14]=[N:13]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[F:9][C:8]([F:11])([F:10])[C:4]1[N:3]=[C:2]([N:12]2[CH:16]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:14]=[N:13]2)[CH:7]=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 200966762-Iodo-6-(trifluoromethyl)pyrazine

Product 1

HCID 71086736HCID 71086736, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

Under N2, 2-iodo-6-(trifluoromethyl)pyrazine (CAS 141492-94-6) (0.137 g, 500 μmol, Eq: 1.00), ethyl 1H-pyrazole-4-carboxylate (CAS 37622-90-5) (70.1 mg, 500 μmol, Eq: 1.00) and potassium carbonate (138 mg, 1.00 mmol, Eq: 2) were combined in DMSO (2.4 ml). The orange solution was stirred at 120° C. over 1 hour. Control with TLC: the reaction was finished. At RT, the RM was partitioned between water and EtOAc; extracted; the organic layer was washed with water and brine; dried over MgSO4; filtered; concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 20 g, 5% to 25% EtOAc in heptane).

Workup

  1. customAt RT, the RM was partitioned between water and EtOAc
  2. extractionextracted
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography (silica gel, 20 g, 5% to 25% EtOAc in heptane)

Sources & evidence

ORD record
ord-cba802a23ee640eaa0c74dfa4191bb1d
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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