2-Bromopropane → HCID 68581136, compound

HRID 2235577Notes

Reaction equation

HRID 2235577 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[C:5]2[C:8]([NH:12][C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]=1.[H-].[Na+].Br[CH:24]([CH3:26])[CH3:25]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:1][C:2]1[N:6]([CH3:7])[C:5]2[C:8]([N:12]([CH:24]([CH3:26])[CH3:25])[C:13]3[CH:14]=[CH:15][C:16]([C:17]#[N:18])=[CH:19][CH:20]=3)=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 68582683HCID 68582683, compound

Product 1

HCID 68581136HCID 68581136, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Procedure

To a suspension of 4-[(2-chloro-1-methyl-1H-benzimidazol-7-yl)amino]benzonitrile (64 mg, 0.226 mmol), tetrabutylammonium iodide (8.4 mg, 0.023 mmol) and sodium hydride (18.1 mg, 0.679 mmol, 90% dry) was added 2-bromopropane (0.07231 ml, 0.679 mmol), and the mixture was stirred at room temperature for 12 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel eluting with a solution of 50% hexane/ethyl acetate to give 64 mg (84%) of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with a solution of 50% hexane/ethyl acetate

Sources & evidence

ORD record
ord-bb707dd7e25b4cf290efec6d3eb10488
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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