Acetonitrile → 4-(4-Fluorophenyl)-1-[(2-methyl-1H-imidazol-1-yl)sulfonyl]-1,2,3,6-tetrahydropyridine

HRID 724729Notes

Reaction equation

HRID 724729 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH:14]=2)=[CH:5][CH:4]=1.FC(F)(F)S([O-])(=O)=O.[CH3:23][C:24]1[N:25]([S:30](N2C=CN=C2C)(=[O:32])=[O:31])[CH:26]=[CH:27][N+:28]=1C.C(#N)C.C(N(CC)CC)C>O>[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:14][CH2:13][N:12]([S:30]([N:25]3[CH:26]=[CH:27][N:28]=[C:24]3[CH3:23])(=[O:32])=[O:31])[CH2:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 1977474-(4-Fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochlorideHCID 108728322,3-dimethyl-1-[(2-methyl-1H-imidazol-1-yl)sulfonyl]-1H-imidazol-3-ium trifluoromethanesulfonate

Product 1

HCID 218786854-(4-Fluorophenyl)-1-[(2-methyl-1H-imidazol-1-yl)sulfonyl]-1,2,3,6-tetrahydropyridineYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride (150 mg, 700 μmol), 2,3-dimethyl-1-[(2-methyl-1H-imidazol-1-yl)sulfonyl]-1H-imidazol-3-ium trifluoromethanesulfonate (410 mg, 1.05 mmol), acetonitrile (5 mL) and triethylamine (98 μL, 700 μmol) was stirred at 25° C. for 24 h. The reaction was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by preparative LCMS to yield the desired product (117 mg, 52%). MF=C15H16FN3O2S; LCMS found for C15H17FN3O2S(M+H)+: m/z=322.

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by preparative LCMS

Sources & evidence

ORD record
ord-43b866aa4e534fa891134f373c1754f0
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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