Potassium Carbonate → HCID 12056720, compound

HRID 1060525Notes

Reaction equation

HRID 1060525 reaction equation
Br[CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[N:4]=1.[F:20][C:21]([F:28])([F:27])[C:22]1[CH:26]=[CH:25][NH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:9][C:8]1[C:3]([CH2:2][N:24]2[CH:25]=[CH:26][C:22]([C:21]([F:28])([F:27])[F:20])=[N:23]2)=[N:4][C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18070343-(Trifluoromethyl)pyrazoleHCID 12056719HCID 12056719, compound

Product 1

HCID 12056720HCID 12056720, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound of Step C (0.7 g, 2 mmol), 3-trifluoromethylpyrazole (0.27 g, 2 mmol) and potassium carbonate (0.83 g, 6 mmol) were suspended in 10 mL of acetonitrile and heated to reflux for 1 h. The salts were filtered and the acetonitrile was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with hexanes/ethyl acetate (85:15) to afford 0.52 g of the title compound of Step D, a compound of this invention, as a white solid melting at 112-114° C. 1H NMR (CDCl3): δ2.39 (s, 3H), 5.53 (s, 2H), 6.62 (d, 1H), 7.6-7.8 (m, 3H), 8.44 (d, 2H), 8.6 (s, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. filtrationThe salts were filtered
  4. customthe acetonitrile was removed under reduced pressure
  5. customThe residue was purified by chromatography on silica gel eluting with hexanes/ethyl acetate (85:15)

Sources & evidence

ORD record
ord-1e03e9c77e2e4ba0add5b6e52e92212f
Source dataset
uspto-grants-2003_02
Patent number
US06525001B1

Reaction notes

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