1-Methyl-1H-imidazole-4-carbonitrile → ethyl 4-(4-cyano-1-methyl-1H-imidazol-5-yl)-1-ethyl-1H-pyrrole-2-carboxylate

HRID 1082893

Reaction equation

HRID 1082893 reaction equation
CCOC(=O)c1cc(Br)cn1CC.Cn1cnc(C#N)c1>C=C[CH2][Pd][Cl].C=C[CH2][Pd][Cl].CC(=O)N(C)C.CC(C)(C)C(=O)[O-].CN(C)c1ccc(P(C2CCCCC2)C2CCCCC2)cc1.[K+]>CCOC(=O)c1cc(-c2c(C#N)ncn2C)cn1CC

Participants

8

Reactant 2

HCID 27951151-Methyl-1H-imidazole-4-carbonitrileHCID 78918332Ethyl 4-bromo-1-ethyl-1H-pyrrole-2-carboxylate

Product 1

HCID 117937785ethyl 4-(4-cyano-1-methyl-1H-imidazol-5-yl)-1-ethyl-1H-pyrrole-2-carboxylateYield 10.35%

Reagents, catalysts & solvents 5

HCID 23662159Potassium TrimethylacetateReagentHCID 142458Benzenamine, 4-(dicyclohexylphosphino)-N,N-dimethyl-CatalystHCID 178455864HCID 178455864, compoundCatalystHCID 31374DimethylacetamideSolvent3×HCID 741954,4'-Bis(1,1-dimethylethyl)-1,1'-biphenylInternal standard

Conditions

Temperature
120 °C

Workup

  1. temperatureCool to room temperature
  2. additionNo procedure recorded
  3. aliquotNo procedure recorded
  4. filtrationFilter into HPLC analysis plate · Keep liquid/mobile
  5. washwash filter with 400 microliter of acetonitrile/water (4:1)

Sources & evidence

ORD record
ord-0b71c7a1c6dd4a6a8cf4ff4fa338d963
Source dataset
Pd-catalyzed C-H arylation of imidazole with aryl bromide
Original link
View source

Linked notes

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