Ammonia → HCID 66961248, compound

HRID 1362754Notes

Reaction equation

HRID 1362754 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][C:5]([N:9]2[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]2)=[C:4]([O:15][CH3:16])[CH:3]=1.[NH3:17].[C:18](OCC)(=O)C>CN(C=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:8][C:7]1[CH:6]=[C:5]([N:9]2[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]2)[C:4]([O:15][CH3:16])=[CH:3][C:2]=1[C:18]#[N:17]

Participants

8

Reactant 3

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 669608761-(4-bromo-5-fluoro-2-methoxyphenyl)-4-methyl-1H-imidazole

Product 1

HCID 66961248HCID 66961248, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst2×HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst2×HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Zinc cyanide (4.05 g), tris(dibenzylideneacetone)dipalladium (527 mg) and 1,1′-bis(diphenylphosphino)ferrocene (638 mg) were added to a solution of 1-(4-bromo-5-fluoro-2-methoxyphenyl)-4-methyl-1H-imidazole (16.7 g) obtained in Example 18 in DMF (100 mL) at room temperature, and the reaction solution was stirred with heat in a nitrogen atmosphere at 120° C. for 7 hours. Further, zinc cyanide (4.05 g), tris(dibenzylideneacetone)dipalladium (527 mg) and 1,1′-bis(diphenylphosphino)ferrocene (638 mg) were added to the reaction solution, and the reaction solution was stirred with heat for 7 hours. After allowing the reaction solution to be cooled, concentrated aqueous ammonia and ethyl acetate were added to the reaction solution and the organic layer was partitioned. The resulting organic layer was washed with brine, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to obtain 9.5 g of the title compound. Properties data of the compound are as follows.

Workup

  1. stirringthe reaction solution was stirred
  2. temperaturewith heat for 7 hours
  3. temperatureto be cooled
  4. customthe organic layer was partitioned
  5. washThe resulting organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-668731bd8c744365b54018d9d25097a7
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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