2-Chloropyridine → 3-(1-Benzofuran-2-YL)pyridine

HRID 363970Notes

Reaction equation

HRID 363970 reaction equation
Clc1ccccn1.OB(O)c1cc2ccccc2o1>C1CCC2=NCCCN2CC1.C1CCOC1.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.Nc1ccccc1-c1cccc[c]1[Pd][Cl].O>c1cncc(-c2cc3ccccc3o2)c1

Participants

10

Reactant 2

HCID 79772-ChloropyridineHCID 2776266Benzo[b]furan-2-boronic acid

Product 1

HCID 218560443-(1-Benzofuran-2-YL)pyridineYield 43.9%

Reagents, catalysts & solvents 7

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneReagentHCID 178439015HCID 178439015, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent5×HCID 180AcetoneWorkupHCID 931NaphthaleneInternal standardHCID 962WaterWorkup

Conditions

Temperature
110 °C

Workup

  1. additionAs soon as the slug leaves the reactor and is detected at PS2,a quench solution volume equal to the reaction slug volume(prepared slug volume + base injection volume) is injected into the reaction slug

Sources & evidence

ORD record
ord-515c719daf9141c4b79c882179e36619
Source dataset
Reizman Suzuki Cross-Coupling
Original link
View source

Reaction notes

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