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

HRID 1082911Notes

Reaction equation

HRID 1082911 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-].[K+].c1ccc(-c2nn(-c3ccccc3)c(-c3ccccc3)c2-n2nccc2P(C2CCCCC2)C2CCCCC2)cc1>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 14.37%

Reagents, catalysts & solvents 5

HCID 23662159Potassium TrimethylacetateReagentHCID 534309145-(Dicyclohexylphosphino)-1',3',5'-triphenyl-[1,4']-bi-1H-pyrazoleCatalystHCID 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-c3763d23bb0b4f10b66c241331141395
Source dataset
Pd-catalyzed C-H arylation of imidazole with aryl bromide
Original link
View source

Reaction notes

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