Dimethyl Sulfoxide → 1-(2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}phenyl)-1H-imidazole

HRID 735372Notes

Reaction equation

HRID 735372 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4F)(=[O:20])=[O:19])[CH:14]=3)[CH:9]=2)=[CH:4][CH:3]=1.[NH:28]1[CH:32]=[CH:31][N:30]=[CH:29]1.[C:33](=[O:36])([O-])[O-:34].[K+].[K+].CS(C)=O>O>[C:33]([O:34][CH2:26][CH3:21])(=[O:36])[CH3:29].[CH3:2][CH2:3][CH2:4][CH:5]([CH3:8])[CH3:6].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)(=[O:19])=[O:20])[CH:12]=[CH:11]3)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 795ImidazoleHCID 11430Potassium CarbonateHCID 689024302-(4-Fluorophenyl)-6-[(2-fluorophenyl)sulfonyl]naphthalene

Product 2

HCID 21882781Isohexane ethyl acetateYield 80%HCID 689003161-(2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}phenyl)-1H-imidazoleYield 167.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(4-fluorophenyl)-6-[(2-fluorophenyl)sulfonyl]naphthalene (110 mg, 0.29 mmol), imidazole (30 mg, 0.44 mmol), potassium carbonate (100 mg, 0.72 mmol) and dimethyl sulfoxide (1.5 mL) was reacted in a microwave at 150° C. for 20 minutes. The mixture was poured into water (100 mL) and extracted with ethyl acetate (2×50 mL). These extracts were washed with water and saturated brine then dried (MgSO4), filtered and solvent removed in vacuo. Purification by flash column chromatography eluting with 40% ethyl acetate/isohexane then 80% ethyl acetate/isohexane gave 1-(2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}phenyl)-1H-imidazole (104 mg, 84%). 1H NMR (500 MHz, CDCl3) δ 8.55 (1H, dd, J=1.7, 7.8 Hz), 7.96 (1H, s), 7.91 (1H, d, J=8.6 Hz), 7.89 (1H, s), 7.83 (1H, d, J=8.7 Hz), 7.80 (1H, dd, J=1.7, 8.5 Hz), 7.75-7.65 (4H, m), 7.42 (1H, dd, J=1.8, 8.6 Hz), 7.29 (1H, s), 7.23-7.17 (3H, m), 6.97 (1H, s), 6.75 (1H, s); m/z (ES+) 429 [MH+].

Workup

  1. customwas reacted in a microwave at 150° C. for 20 minutes
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washThese extracts were washed with water and saturated brine
  4. dry with materialthen dried (MgSO4)
  5. filtrationfiltered
  6. customsolvent removed in vacuo
  7. customPurification by flash column chromatography
  8. washeluting with 40% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-78664b199bc0439c875f04256079e353
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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