3-Bromoquinoline → 3,5-Dimethyl-4-quinolin-3-yl-1,2-oxazole

HRID 476424Notes

Reaction equation

HRID 476424 reaction equation
Brc1cnc2ccccc2c1.Cc1noc(C)c1B1OC(C)(C)C(C)(C)O1>C1CCC2=NCCCN2CC1.C1CCOC1.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CS(=O)(=O)[O][Pd][c]1ccccc1-c1ccccc1N.O>Cc1noc(C)c1-c1cnc2ccccc2c1

Participants

10

Reactant 2

HCID 214133-BromoquinolineHCID 27586563,5-Dimethylisoxazole-4-boronic acid pinacol ester

Product 1

HCID 442435543,5-Dimethyl-4-quinolin-3-yl-1,2-oxazoleYield 60.2%

Reagents, catalysts & solvents 7

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneReagentHCID 178439014HCID 178439014, 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-3938c82b458d4a97935e20f74d1739e3
Source dataset
Reizman Suzuki Cross-Coupling
Original link
View source

Reaction notes

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