Potassium Carbonate → HCID 67135491, compound

HRID 2174631Notes

Reaction equation

HRID 2174631 reaction equation
[CH3:1][N:2]1[C:6]([OH:7])=[C:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([F:15])=[CH:10][C:9]=2[F:16])[C:4]([CH3:17])=[N:3]1.[F:18][C:19]1[CH:20]=[C:21]([N+:27]([O-:29])=[O:28])[CH:22]=[C:23]([F:26])[C:24]=1F.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[F:18][C:19]1[CH:20]=[C:21]([N+:27]([O-:29])=[O:28])[CH:22]=[C:23]([F:26])[C:24]=1[O:7][C:6]1[N:2]([CH3:1])[N:3]=[C:4]([CH3:17])[C:5]=1[C:8]1[C:13]([F:14])=[CH:12][C:11]([F:15])=[CH:10][C:9]=1[F:16]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27827931,2,3-Trifluoro-5-nitrobenzeneHCID 178434066HCID 178434066, compound2×

Product 1

HCID 67135491HCID 67135491, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1,3-Dimethyl-4-(2,4,6-trifluorophenyl)-1H-pyrazol-5-ol (i.e. the product of Step C) (0.310 g, 1.28 mmol), was combined with 3,4,5-trifluoronitrobenzene (157 μL, 1.35 mmol) and potassium carbonate powder (0.27 g, 2 mmol) in dry N,N-dimethylformamide (4 mL). This mixture was stirred and heated at 80° C. for 45 minutes and then allowed to cool. The reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (2×10 mL). The organic phase was washed with water and with brine, dried over MgSO4, and concentrated to leave a viscous residue. This residue was purified by column chromatography through silica gel eluted with a gradient of ethyl acetate (30% to 100%) in hexane to give the title product, a compound of the present invention, as an off-white solid (209 mg).

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. washThe organic phase was washed with water and with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto leave a viscous residue
  7. customThis residue was purified by column chromatography through silica gel
  8. washeluted with a gradient of ethyl acetate (30% to 100%) in hexane

Sources & evidence

ORD record
ord-4e76465fa025402087e9aa05a8b32283
Source dataset
uspto-grants-2015_06
Patent number
US09062005B2

Reaction notes

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