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

Reaction equation

Cn1cnc(C#N)c1.Fc1ccccc1Br>C=C[CH2-].C=C[CH2-].CC(=O)N(C)C.CC(=O)[O-].C[C@]12C[C@@]3(C)O[C@](C)(C[C@@](C)(O1)P3c1ccccc1)O2.[Cl][Pd+].[Cl][Pd+].[K+]>Cn1cnc(C#N)c1-c1ccccc1F

Participants

Conditions

Temperature: 90 °C

Workup

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
stirringNo procedure recorded
aliquotNo procedure recorded
filtrationKeep organic

Sources & evidence

ORD record: ord-40463c0ec18d4e278a896f72be7a9528
Source dataset: Shields Arylation

Reaction notes

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Participants

Reactant 2

HCID 612591-Bromo-2-fluorobenzene

HCID 27951151-Methyl-1H-imidazole-4-carbonitrile

Product 2

HCID 741954,4'-Bis(1,1-dimethylethyl)-1,1'-biphenyl

HCID 841174465-(2-Fluorophenyl)-1-methylimidazole-4-carbonitrileYield 13.19%

Reagents, catalysts & solvents 5

HCID 517044Potassium AcetateReagent

HCID 61538Palladium, di-mu-chlorobis(eta3-2-propenyl)di-Catalyst

HCID 71669129HCID 71669129, compoundCatalyst

HCID 31374DimethylacetamideSolvent

HCID 741954,4'-Bis(1,1-dimethylethyl)-1,1'-biphenylInternal standard

Conditions

Temperature: 90 °C

Workup

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
stirringNo procedure recorded
aliquotNo procedure recorded
filtrationKeep organic

Sources & evidence

ORD record: ord-40463c0ec18d4e278a896f72be7a9528
Source dataset: Shields Arylation

Reaction notes

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