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

HRID 1166367Notes

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

Participants

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

customthe solvent was removed under reduced pressure
dissolutionredissolved in 50 ml of methylene chloride
extractionextracted with 50 ml of an aqueous solution of sodium bicarbonate
dry with materialThe organic extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated
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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