Methyl iodide → HCID 44553222, compound

HRID 1254029Notes

Reaction equation

HRID 1254029 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[NH:13][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:30]I>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:30])[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:20]2[CH:21]=[CH:22][C:23]([C:24]#[N:25])=[CH:26][CH:27]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178509630HCID 178509630, compound

Product 1

HCID 44553222HCID 44553222, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-{5-[(4-Chlorophenyl)thio]-2-phenyl-1H-imidazol-4-yl}benzonitrile (Example 1, 222 mg, 0.57 mmol) was dissolve in THF (6 mL), to which was added NaH (60% wt, 27.5 mg, 0.687 mmol) at 0° C. After stirring for 5 min, MeI (0.05 mL, 0.86 mmol) was added. The reaction was stirred at 0° C. for 2 h, and then quenched with aq NH4Cl to adjust the pH to 6-8. The product was extracted with EtOAc and the organic layer was washed with water, brine, dried over MgSO4, filtered, and concentrated. The residue was subject to silica column chromatography (0-20% EtOAc in hexanes) to give the title compound as the major region isomer. 1H NMR (500 MHz, (CD3OD): 8.18 (d, 2H), 7.77 (m, 2H), 7.76 (d, 2H), 7.68 (m, 3H), 7.34 (d, 2H), 7.09 (d, 2H), 3.70 (s, 3H). LCMS: m/z 402 (M+H)+. The minor region isomer was the title compound of Example 3.

Workup

  1. customat 0° C
  2. stirringThe reaction was stirred at 0° C. for 2 h
  3. customquenched with aq NH4Cl
  4. extractionThe product was extracted with EtOAc
  5. washthe organic layer was washed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-42ab9e9eca1c424b838c18ea68c408f6
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

Loading…