Methyl iodide → Methyl 2-(1-(bis(4-methoxyphenyl)methyl)-3-methyl-2-oxo-2,3-dihydro-1h-benzo[d]imidazol-4-yloxy)-4-fluorobenzoate

HRID 1848916Notes

Reaction equation

HRID 1848916 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([O:19][C:20]4[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:21]=4[C:22]([O:24][CH3:25])=[O:23])[C:13]=3[NH:12][C:11]2=[O:31])=[CH:5][CH:4]=1.[H-].[Na+].I[CH3:43]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:32]2[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=2)[N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([O:19][C:20]4[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:21]=4[C:22]([O:24][CH3:25])=[O:23])[C:13]=3[N:12]([CH3:43])[C:11]2=[O:31])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67227808Methyl 2-(1-(bis(4-methoxyphenyl)methyl)-2-oxo-2,3-dihydro-1h-benzo[d]imidazol-4-yloxy)-4-fluorobenzoate

Product 1

HCID 67227674Methyl 2-(1-(bis(4-methoxyphenyl)methyl)-3-methyl-2-oxo-2,3-dihydro-1h-benzo[d]imidazol-4-yloxy)-4-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of EXAMPLE 368D (250 mg) in anhydrous N,N-dimethylformamide (6 mL) was added sodium hydride (34.1 mg). The mixture was stirred at 50° C. for 30 minutes. Then, iodomethane (35.6 μl) was added and the mixture was stirred at 50° C. overnight. The reaction mixture was quenched with water (30 mL), then extracted with ethyl acetate. The solution was dried (MgSO4), filtered and concentrated to give the title compound.

Workup

  1. stirringthe mixture was stirred at 50° C. overnight
  2. customThe reaction mixture was quenched with water (30 mL)
  3. extractionextracted with ethyl acetate
  4. dry with materialThe solution was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a6e426dd0f3049feb58388cf7dd45699
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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