Methyl iodide → HCID 66690413, compound

HRID 592322Notes

Reaction equation

HRID 592322 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[N:15]=[C:14]([CH:17]([CH3:19])[CH3:18])[NH:13][C:12]=3[CH:11]=[C:10]([C:20]([O:22][CH3:23])=[O:21])[CH:9]=2)=[CH:4][CH:3]=1.[C:24](=O)([O-])[O-].[Cs+].[Cs+].IC>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]([CH:17]([CH3:19])[CH3:18])[N:13]([CH3:24])[C:12]=3[CH:11]=[C:10]([C:20]([O:22][CH3:23])=[O:21])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 66689988HCID 66689988, compound

Product 1

HCID 66690413HCID 66690413, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-(4-fluorophenyl)-2-isopropyl-1H-benzimidazole-6-carboxylate (10.0 mg, 32.0 μmol) and cesium carbonate (26.1 mg, 80.0 μmol) in N,N-dimethylformamide (64 μL) was added iodomethane (3.0 μL, 48.0 μmol). The mixture was stirred at ambient temperature for 15 min. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (6.4 mg): LC-MS [M+1]=327.1.

Workup

  1. customPurification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-7dc3082743b24f638cf900e353182d90
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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