Methyl iodide → HCID 67362640, compound

HRID 1916606Notes

Reaction equation

HRID 1916606 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Br:7][C:8]1[CH:24]=[CH:23][C:11]2[N:12]([CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[C:13](=[O:15])[NH:14][C:10]=2[CH:9]=1.IC.C([O-])(O)=O.[Na+]>CS(C)=O>[Br:7][C:8]1[CH:24]=[CH:23][C:11]2[N:12]([CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[C:13](=[O:15])[N:14]([CH3:1])[C:10]=2[CH:9]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 67363416HCID 67363416, compound

Product 1

HCID 67362640HCID 67362640, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

73 mg (0.65 mmol) potassium-tert-butoxide are added to a solution of 200 mg (0.65 mmol) 5-bromo-1-(2-pyrrolidin-1-yl-ethyl)-1,3-dihydro-benzimidazol-2-one in 4 mL DMSO at RT. The reaction solution is stirred for 30 min and then 40 μL (0.65 mmol) iodomethane are added and stirred for a further 30 min. The mixture is combined with semisaturated NaHCO3 solution and the aqueous phase is extracted twice with 30 mL EtOAc. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac.

Workup

  1. stirringstirred for a further 30 min
  2. extractionthe aqueous phase is extracted twice with 30 mL EtOAc
  3. dry with materialThe organic phase is dried over MgSO4

Sources & evidence

ORD record
ord-609293041d3a4c9fa98dc33edc0f385f
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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