Potassium Carbonate → HCID 58542011, compound

HRID 1966761Notes

Reaction equation

HRID 1966761 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:13])[C:5]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:6][CH:7]=1.[CH:14]([C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19])=O.OOS([O-])=O.[K+].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([C:9]([CH3:10])([CH3:12])[CH3:11])[C:14]([C:16]3[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=3[C:18]#[N:19])=[N:13][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 1012092-CyanobenzaldehydeHCID 23707502Potassium hydroxy sulfiteHCID 43148635HCID 43148635, compound

Product 1

HCID 58542011HCID 58542011, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-N1-tert-butyl-benzene-1,2-diamine (500 mg, 2.06 mmol) in DMF (20 mL) is added 2-formyl-benzonitrile (270 mg, 2.06 mmol) at room temperature. Oxone (758 mg, 1.23 mmol) is added and the solution is stirred at the same temperature for 2 hours. The reaction mixture is poured into 0.5 M K2CO3 solution (30 mL). The product is extracted into EtOAc (3×) and the combined organics are then dried (Na2SO4), filtered, and concentrated. Purification via flash chromatography (25 g silica gel, 0-4% MeOH/CH2Cl2) affords 2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-benzonitrile (765 mg, 100%).

Workup

  1. extractionThe product is extracted into EtOAc (3×)
  2. dry with materialthe combined organics are then dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification via flash chromatography (25 g silica gel, 0-4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-66e88a27bc0a4f3d8fb913b7b3b8c4ce
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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