Sodium hydride → 2-[1-(4-bromo-2-fluorobenzyl)-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl]benzonitrile

HRID 882202Notes

Reaction equation

HRID 882202 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[C:13]#[N:14])[CH:9]=[CH:10][C:5]=2[NH:4][C:3]1=[O:19].[H-].[Na+].[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[C:25]([F:31])[CH:24]=1>CN(C=O)C>[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][N:4]2[C:5]3[CH:10]=[CH:9][C:8]([C:11]4[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=4[C:13]#[N:14])=[CH:7][C:6]=3[N:2]([CH3:1])[C:3]2=[O:19])=[C:25]([F:31])[CH:24]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27336604-Bromo-2-fluorobenzyl bromideHCID 667501612-(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)benzonitrile

Product 1

HCID 680466682-[1-(4-bromo-2-fluorobenzyl)-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl]benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)benzonitrile (6-4, 20 mg, 0.08 mmol) in anhydrous DMF (1 ml) was charged with Sodium Hydride (6.42 mg, 0.16 mmol, 2.0 eq) and 4-Bromo-2-fluorobenzyl bromide (42.5 mg, 0.16 mmol, 2.0 eq). The resulting dark mixture was irradiated in a microwave at 200 deg C. for 15 min, then quenched with water, filtered and purified via reverse-phase HPLC (Acetonitrile/Water gradient with 0.1% TFA present) to afford the title compound, 2-[1-(4-bromo-2-fluorobenzyl)-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl]benzonitrile (6-5), as an orange-tan solid-oil. LRMS m/z: Calc'd for C22H15BrFN3O (M+H) 436.0, found 435.9.

Workup

  1. customThe resulting dark mixture was irradiated in a microwave at 200 deg C
  2. customquenched with water
  3. filtrationfiltered
  4. custompurified via reverse-phase HPLC (Acetonitrile/Water gradient with 0.1% TFA present)

Sources & evidence

ORD record
ord-5cb1a4aec36945eaa3936b2e0407582b
Source dataset
uspto-grants-2015_03
Patent number
US08993779B2

Reaction notes

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