m-Formylbenzonitrile → HCID 58541913, compound

HRID 1966742Notes

Reaction equation

HRID 1966742 reaction equation
[C:1]([NH:5][C:6]1[C:7]([NH2:20])=[CH:8][C:9]([C:12]2[CH:13]=[N:14][CH:15]=[C:16]([O:18][CH3:19])[CH:17]=2)=[CH:10][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH:21]([C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[C:26]#[N:27])=O.OOS([O-])=O.[K+]>CN(C=O)C.O>[C:1]([N:5]1[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([O:18][CH3:19])[CH:17]=3)=[CH:8][C:7]=2[N:20]=[C:21]1[C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[C:26]#[N:27])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 90670m-FormylbenzonitrileHCID 23707502Potassium hydroxy sulfiteHCID 58542005HCID 58542005, compound

Product 1

HCID 58541913HCID 58541913, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N1-tert-Butyl-4-(5-methoxy-pyridin-3-yl)-benzene-1,2-diamine (0.630 g, 2.32 mmol) is dissolved in DMF (5 mL) and water (1 mL). To this solution is added 3-formyl-benzonitrile (0.315 g, 2.40 mmol), followed by Oxone (1.54 g, 2.50 mmol). This reaction mixture is sonicated at room temperature for 1 hour. The solvent is removed in vacuum. The residue is partitioned between EtOAc (3×10 mL) and saturated sodium bicarbonate solution (10 mL). The organic layer is washed with brine, dried over sodium sulfate and is filtered. The filtrate is concentrated and the residue is purified by flash chromatography (40 g silica gel, eluted with 0-100% EtOAc in hexane) to give 3-[1-tert-butyl-5-(5-methoxy-pyridin-3-yl)-1H-benzimidazol-2-yl]-benzonitrile (0.575 g, 65%) as a white solid.

Workup

  1. customThis reaction mixture is sonicated at room temperature for 1 hour
  2. customThe solvent is removed in vacuum
  3. customThe residue is partitioned between EtOAc (3×10 mL) and saturated sodium bicarbonate solution (10 mL)
  4. washThe organic layer is washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationis filtered
  7. concentrationThe filtrate is concentrated
  8. customthe residue is purified by flash chromatography (40 g silica gel, eluted with 0-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-08cf0129069841299ea96f38f0949dac
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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