Methyl iodide → HCID 59171008, compound

HRID 1362704Notes

Reaction equation

HRID 1362704 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([N:13]2[CH2:18][CH2:17][CH2:16]/[C:15](=[CH:19]\[C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]4)=[C:22]([O:32][CH3:33])[CH:21]=3)/[C:14]2=[O:34])[CH2:11][OH:12])=[CH:6][CH:5]=1.CI.O.[C:38](=O)(O)[O-].[Na+]>C1COCC1.C(OCC)(=O)C>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([N:13]2[CH2:18][CH2:17][CH2:16]/[C:15](=[CH:19]\[C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]4)=[C:22]([O:32][CH3:33])[CH:21]=3)/[C:14]2=[O:34])[CH2:11][O:12][CH3:38])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66961185HCID 66961185, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 59171008HCID 59171008, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (containing mineral oil at 40%, 24 mg) was added to a solution of (E)-1-(1-(4-fluorophenyl)-2-hydroxyethyl)-3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)piperidin-2-one synthesized by the method described in Example 629 (216 mg) in THF (5 mL), and the reaction solution was stirred at room temperature for 50 minutes. Then, methyl iodide (85 mg) was added to the reaction solution, and the reaction solution was stirred at room temperature for 14 hours. Saturated sodium bicarbonate water and ethyl acetate were added to the reaction solution and the organic layer was partitioned. The resulting organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Carrier: Chromatorex™ NH, elution solvent: heptane:ethyl acetate=1:1->ethyl acetate) to obtain 185 mg of the title compound. The physical properties of the compound are as follows.

Workup

  1. customsynthesized by the method
  2. stirringthe reaction solution was stirred at room temperature for 14 hours
  3. customthe organic layer was partitioned
  4. dry with materialThe resulting organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (Carrier: Chromatorex™ NH, elution solvent: heptane:ethyl acetate=1:1->ethyl acetate)

Sources & evidence

ORD record
ord-bbd67cb929924921b448d3b4681b3678
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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