Dimethylformamide → HCID 178509930, compound

HRID 505523Notes

Reaction equation

HRID 505523 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]=[N:12][NH:11][C:10]=2[CH:9]=[CH:8][C:7]=1[Cl:15].[CH3:20][N:21](C=O)C>CCOC(C)=O.[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]=[N:12][NH:11][C:10]=3[CH:9]=[CH:8][C:7]=2[Cl:15])[CH:16]=1)[C:20]#[N:21]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 1784778354-(3-bromo-5-chlorophenoxy)-5-chloro-1H-1,2,3-benzotriazole

Product 1

HCID 178509930HCID 178509930, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-(3-bromo-5-chlorophenoxy)-5-chloro-1H-1,2,3-benzotriazole (5.0 g, 14 mmol), tetrakis triphenylphosphine palladium (0) (4.83 g, 4.83 mmol) and zinc cyanide (1.96 g, 16.7 mmol) were suspended in dry DMF (50 mL) under N2 and placed in an oil bath at 90° C. After 2.5 hours, the reaction was allowed to cool to room temperature. The mixture was diluted with EtOAc (300 mL) and washed with water (4×100 mL), dried (MgSO4), filtered and concentrated with silica gel (20 g). This was purified by automated column chromatography on silica gel (120 g), eluting with 0-30% EtOAc/hexanes to deliver the title compound. LRMS (M+1)=304.8.

Workup

  1. customplaced in an oil bath at 90° C
  2. washwashed with water (4×100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated with silica gel (20 g)
  6. customThis was purified by automated column chromatography on silica gel (120 g)
  7. washeluting with 0-30% EtOAc/hexanes

Sources & evidence

ORD record
ord-ca405af8e237421d88ecbd04e65b6f9d
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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