Dimethylformamide → 3-chloro-5-[(5-chloro-1H-benzimidazol-4-yl)oxy]benzonitrile

HRID 505530Notes

Reaction equation

HRID 505530 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[O:5][C:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[CH:9]=[CH:8][C:7]=1[Cl:15].[CH3:20][N:21](C=O)C>[C-]#N.[Zn+2].[C-]#N>[Cl:19][C:17]1[CH:18]=[C:2]([CH:3]=[C:4]([O:5][C:6]2[C:14]3[N:13]=[CH:12][NH:11][C:10]=3[CH:9]=[CH:8][C:7]=2[Cl:15])[CH:16]=1)[C:20]#[N:21]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 684281464-(3-bromo-5-chlorophenoxy)-5-chloro-1H-benzimidazole

Product 1

HCID 684255163-chloro-5-[(5-chloro-1H-benzimidazol-4-yl)oxy]benzonitrile

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
90 °C

Procedure

To a solution of 4-(3-bromo-5-chlorophenoxy)-5-chloro-1H-benzimidazole 430 mg, 1.201 mmol) in DMF (5 mL) was added palladium tetrakistriphenylphosphine (416 mg, 0.360 mmol) and zinc cyanide (141 mg, 1.201 mmol) and the mixture heated to 90° C. for 1 hour. This mixture was partitioned between ethyl acetate (50 mL) and water (20 mL). The organic extract was washed with water (10 mL), dried over MgSO4, filtered and the solvent removed in vacuo. This residue was purified on silica gel eluting with 0-20% ethyl acetate/methylene chloride to give the title compound. LRMS (M+1)=303.8.

Workup

  1. customThis mixture was partitioned between ethyl acetate (50 mL) and water (20 mL)
  2. extractionThe organic extract
  3. washwas washed with water (10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThis residue was purified on silica gel eluting with 0-20% ethyl acetate/methylene chloride

Sources & evidence

ORD record
ord-8c095fb122ad4b939930000fcd8dab0d
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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