Potassium Carbonate → HCID 67111088, compound

HRID 540789Notes

Reaction equation

HRID 540789 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:12][N:11]([CH2:13][CH2:14][OH:15])[C:10](=[O:16])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[F:17][C:18]([F:27])([F:26])[C:19]1[CH:24]=[CH:23][C:22](F)=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([O:16][C:22]3[CH:23]=[CH:24][C:19]([C:18]([F:27])([F:26])[F:17])=[CH:20][CH:21]=3)[N:11]([CH2:13][CH2:14][OH:15])[N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67873Benzene, 1-fluoro-4-(trifluoromethyl)-2×HCID 67111063HCID 67111063, compound

Product 1

HCID 67111088HCID 67111088, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
160 °C

Procedure

5-(3-Bromophenyl)-2-(2-hydroxyethyl)-1,2-dihydro-3H-pyrazol-3-one (21 g, 74 mmol), 4-trifluoromethyl-1-fluorobenzene (28 mL, 220 mmol), and K2CO3 (30.6 g, 220 mmol) were combined in 140 mL of dry DMA. The mixture was heated at 160° C. with stirring in a sealed vessel for 13 h. The reaction was cooled to ambient temperature and more 4-trifluoromethyl-1-fluorobenzene (5 mL, 39 mmol) was added. The mixture was heated at 160° C. with stirring in a sealed vessel for 18 h. The reaction was cooled to ambient temperature and diluted with EtOAc. The mixture was washed with water and brine, then dried over MgSO4, filtered, and the solvent was removed under reduced pressure. The dark residue was chromatographed on a 330 g silica gel column using 0-40% EtOAc:hexanes over 70 min at 100 mL/min. The product-containing fractions were combined and the solvent was removed under reduced pressure to give 2-{3-(3-bromophenyl)-5-[4-(trifluoromethyl)phenoxy]-1H-pyrazol-1-yl}ethanol as an oil which solidified on standing. Calcd (M−1-1)+: 428.2. Found: 428.3

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. temperatureThe mixture was heated at 160° C.
  3. stirringwith stirring in a sealed vessel for 18 h
  4. temperatureThe reaction was cooled to ambient temperature
  5. washThe mixture was washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customThe dark residue was chromatographed on a 330 g silica gel column
  10. waithexanes over 70 min at 100 mL/min
  11. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4f0fbd8d163242c19bd86dd217b4784b
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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