6-Bromoquinoline → 6-Bromoquinoline

HRID 2259142Notes

Reaction equation

HRID 2259142 reaction equation
Brc1ccc2ncccc2c1.Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O>CC(=O)[O-].CC(=O)[O-].CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CN(C)C=O.O=C([O-])[O-].[Cs+].[Cs+].[Pd+2]>Cc1ccc2c(cnn2C2CCCCO2)c1.Cc1ccc2c(cnn2C2CCCCO2)c1-c1ccc2ncccc2c1.c1ccc2ncccc2c1.c1cnc2ccc(-c3ccc4ncccc4c3)cc2c1

Participants

12

Reactant 2

HCID 792436-BromoquinolineHCID 129009568[5-Methyl-1-(oxan-2-yl)-1H-indazol-4-yl]boronic acid

Product 6

HCID 7047QuinolineYield 5.742%HCID 792436-BromoquinolineYield 51.689%HCID 6207116,6'-BiquinolineYield 15.214%HCID 10751213HCID 10751213, compoundYield 1.94%HCID 129009568[5-Methyl-1-(oxan-2-yl)-1H-indazol-4-yl]boronic acidYield 25.415%HCID 178422846HCID 178422846, compoundYield 0%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 167845palladium(II) acetateCatalystHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Sources & evidence

ORD record
ord-98a82f02b2be4af8ac71fbabc50162cd
Source dataset
HTE Suzuki coupling dataset

Reaction notes

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