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

HRID 476461Notes

Reaction equation

HRID 476461 reaction equation
Brc1cnc2ccccc2c1.Cc1noc(C)c1B1OC(C)(C)C(C)(C)O1>C1CCC2=NCCCN2CC1.C1CCOC1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.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 8.7%

Reagents, catalysts & solvents 7

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneReagentHCID 178422002HCID 178422002, 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-9ab813edc67e4135a2913710f919168d
Source dataset
Reizman Suzuki Cross-Coupling
Original link
View source

Reaction notes

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