1-Bromo-2-fluorobenzene → 5-(2-Fluorophenyl)-1-methylimidazole-4-carbonitrile

HRID 1933910Notes

Reaction equation

HRID 1933910 reaction equation
Cn1cnc(C#N)c1.Fc1ccccc1Br>C=C[CH2-].C=C[CH2-].CC(=O)N(C)C.CC(=O)[O-].CP(C)c1ccccc1.[Cl][Pd+].[Cl][Pd+].[Cs+]>Cn1cnc(C#N)c1-c1ccccc1F

Participants

9

Reactant 2

HCID 612591-Bromo-2-fluorobenzeneHCID 27951151-Methyl-1H-imidazole-4-carbonitrile

Product 2

HCID 741954,4'-Bis(1,1-dimethylethyl)-1,1'-biphenylHCID 841174465-(2-Fluorophenyl)-1-methylimidazole-4-carbonitrileYield 5.9%

Reagents, catalysts & solvents 5

HCID 5152919Cesium acetateReagentHCID 61538Palladium, di-mu-chlorobis(eta3-2-propenyl)di-CatalystHCID 69597DimethylphenylphosphineCatalystHCID 31374DimethylacetamideSolventHCID 741954,4'-Bis(1,1-dimethylethyl)-1,1'-biphenylInternal standard

Conditions

Temperature
120 °C

Workup

  1. additionThe plate was removed from the glovebox, opened, and diluted to a 900 uL total volume with N,N-dimethylacetamide. The plate was stirred for 5 min and a 75 uL sample was taken and filtered into an HPLC analysis plate. The filter was rinsed with 400 uL acetonitrile/water (4:1) solution and analyzed by UHPLCMS
  2. stirringNo procedure recorded
  3. aliquotNo procedure recorded
  4. filtrationKeep organic

Sources & evidence

ORD record
ord-ef60962383b84520aecb1d70d43532bb
Source dataset
Shields Arylation

Reaction notes

Loading…