3-Bromo-1,1,1-trifluoro-2-propanone → 3-methyl-6-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine

HRID 52351Notes

Reaction equation

HRID 52351 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[NH:20])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.C(=O)(O)[O-].[Na+].Br[CH2:27][C:28](=[O:33])[C:29]([F:32])([F:31])[F:30]>C(O)(C)C>[CH3:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[N:9]([C:10]3[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=3)[CH2:27][C:28]([OH:33])([C:29]([F:32])([F:31])[F:30])[N:20]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 516892Sodium BicarbonateHCID 178425635HCID 178425635, compound

Product 1

HCID 199633603-methyl-6-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of the amidine of step 1 (10 mmol and sodium bicarbonate (20 mmol) in isopropanol (150 ml), 3-bromo-1,1,1-trifluoroacetone (15 mmol) is added. After heating at 80°-85° C. for 24 hours, the reaction mixture is cooled and filtered. The residue is washed with methylene chloride and the combined organic fractions are dried over sodium sulfate, filtered and concentrated. The crude mixture is chromatographed on silica gel using mixtures of ethyl acetate, isopropanol and ammonium hydroxide as eluants to give the desired 4,5-dihydro-imidazole

Workup

  1. additionis added
  2. temperatureAfter heating at 80°-85° C. for 24 hours
  3. temperaturethe reaction mixture is cooled
  4. filtrationfiltered
  5. washThe residue is washed with methylene chloride
  6. dry with materialthe combined organic fractions are dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude mixture is chromatographed on silica gel using mixtures of ethyl acetate, isopropanol and ammonium hydroxide as eluants

Sources & evidence

ORD record
ord-316ba6187fd74b6abe45e83fcd3d544a
Source dataset
uspto-grants-1997_04
Patent number
US05616601

Reaction notes

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