Methyl iodide → Methyl 4-(4-fluorophenyl)-2-(2-hydroxy-2-methylpropyl)-1-methyl-1H-benzimidazole-6-carboxylate

HRID 592323Notes

Reaction equation

HRID 592323 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[N:15]=[C:14]([CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])[NH:13][C:12]=3[CH:11]=[C:10]([C:22]([O:24][CH3:25])=[O:23])[CH:9]=2)=[CH:4][CH:3]=1.[C:26](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[N:15]=[C:14]([CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])[N:13]([CH3:26])[C:12]=3[CH:11]=[C:10]([C:22]([O:24][CH3:25])=[O:23])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 66691128methyl 4-(4-fluorophenyl)-2-(2-hydroxy-2-methylpropyl)-1H-benzimidazole-6-carboxylate

Product 1

HCID 66689966Methyl 4-(4-fluorophenyl)-2-(2-hydroxy-2-methylpropyl)-1-methyl-1H-benzimidazole-6-carboxylateYield 30.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-(4-fluorophenyl)-2-(2-hydroxy-2-methylpropyl)-1H-benzimidazole-6-carboxylate (125 mg, 0.365 mmol) and cesium carbonate (297 mg, 0.913 mmol) in N,N-dimethylformamide (0.730 mL) was added methyl iodide (0.025 mL, 0.402 mmol). Stirred at ambient temperature for 2.5 h. Filtered and purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% TFA) gave the title compound (40 mg): LC-MS [M+1]=357.2.

Workup

  1. filtrationFiltered
  2. custompurification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% TFA)

Sources & evidence

ORD record
ord-ea9a52ea930e4bafa82e01a589591c2e
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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