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

HRID 363892Notes

Reaction equation

HRID 363892 reaction equation
Clc1ccccn1.OB(O)c1cc2ccccc2o1>C1CCC2=NCCCN2CC1.C1CCOC1.CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.CS(=O)(=O)[O][Pd][c]1ccccc1-c1ccccc1N.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 86.5%

Reagents, catalysts & solvents 7

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneReagentHCID 178458461HCID 178458461, 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-feecb6de8e3a44a984d0e2d204cc83da
Source dataset
Reizman Suzuki Cross-Coupling
Original link
View source

Reaction notes

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