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Methanol → 5-methyl-2-[1-[4-(methylsulfonyl)phenyl]-4-trifluoromethyl-1H-imidazol-2-yl]pyridine

HRID 1166367
Notes
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Reaction equation

HRID 1166367 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([C:17]3[CH:22]=[CH:21][C:20](SC)=[CH:19][CH:18]=3)[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:12]=2)=[N:6][CH:7]=1.O[O:26][S:27]([O-:29])=O.[K+].[CH3:31]O>O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([C:17]3[CH:22]=[CH:21][C:20]([S:27]([CH3:31])(=[O:29])=[O:26])=[CH:19][CH:18]=3)[CH:10]=[C:11]([C:13]([F:15])([F:14])[F:16])[N:12]=2)=[N:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 22998066HCID 22998066, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 108098545-methyl-2-[1-[4-(methylsulfonyl)phenyl]-4-trifluoromethyl-1H-imidazol-2-yl]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To solution of the methylthio compound from step 4 (3.95 g, 11.5 mmol) in 45 ml of methanol was added an aqueous solution of Oxone® (6.94 g dissolved in 28 ml of water). After stirring at 25° C. for 4-5 hours, the solvent was removed under reduced pressure, redissolved in 50 ml of methylene chloride and extracted with 50 ml of an aqueous solution of sodium bicarbonate. The organic extracts were dried (MgSO4), filtered and concentrated. The crude material was purified by chromatography (silica gel; 50% ethyl acetate/toluene) to provide 1.6 g of the desired product: mp 196° C. Anal Calc'd. for C17H14N3SO2F3: C, 53.54; H, 3.70; N, 11.02; S, 8.41. Found: C, 53.09; H, 3.43; N, 10.75; S, 8.69.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionredissolved in 50 ml of methylene chloride
  3. extractionextracted with 50 ml of an aqueous solution of sodium bicarbonate
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by chromatography (silica gel; 50% ethyl acetate/toluene)

Sources & evidence

ORD record
ord-19bc0ac54e9c4e53b59d8a9597ce8b78
Source dataset
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06613789B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes