Water → HCID 18426846, compound

HRID 1281162Notes

Reaction equation

HRID 1281162 reaction equation
[Cl:1][C:2]1[C:24]([Cl:25])=[CH:23][C:5]2[N:6]([CH2:20][O:21][CH3:22])[C:7]([C:9]3[NH:10][C:11]4[C:16]([CH:17]=3)=[CH:15][C:14]([CH:18]=[O:19])=[CH:13][CH:12]=4)=[N:8][C:4]=2[CH:3]=1.IC.[CH3:28]C(C)([O-])C.[K+].O>CN(C)C=O>[Cl:1][C:2]1[C:24]([Cl:25])=[CH:23][C:5]2[N:6]([CH2:20][O:21][CH3:22])[C:7]([C:9]3[N:10]([CH3:28])[C:11]4[C:16]([CH:17]=3)=[CH:15][C:14]([CH:18]=[O:19])=[CH:13][CH:12]=4)=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 18426817HCID 18426817, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18426846HCID 18426846, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5,6-dichloro-2-[5-formylindol-2-yl]-1-(methoxymethyl)benzimidazole obtained in Example 47 (32 mg, 0.086 mmol) in dimethylformamide (2 mL) were added iodomethane (0.027 mL, 0.43 mmol) and potassium tert-butoxide (19 mg, 0.17 mmol) under nitrogen atmosphere, and the mixture was stirred at room temperature for 18 h. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure to afford 5,6-dichloro-2-[5-formyl-1-methylindol-2-yl]-1-methoxymethylbenzimidazole (30 mg, 90%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ee086154cb3e479cb92e3224d208ea76
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

Loading…