3-Chloropyridine → HCID 44243553, compound

HRID 1745984Notes

Reaction equation

HRID 1745984 reaction equation
Cc1noc(C)c1B1OC(C)(C)C(C)(C)O1.Clc1cccnc1>C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC2=NCCCN2CC1.C1CCOC1.CS(=O)(=O)[O][Pd][c]1ccccc1-c1ccccc1N.O>Cc1noc(C)c1-c1cccnc1

Participants

10

Reactant 2

HCID 122873-ChloropyridineHCID 27586563,5-Dimethylisoxazole-4-boronic acid pinacol ester

Product 1

HCID 44243553HCID 44243553, compoundYield 30.6%

Reagents, catalysts & solvents 7

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneReagentHCID 178420537HCID 178420537, 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-37ce19b013104fed84ef43b0d16f0e42
Source dataset
Reizman Suzuki Cross-Coupling
Original link
View source

Reaction notes

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