6-Bromoquinoline → 6-Bromoquinoline

HRID 2259150Notes

Reaction equation

HRID 2259150 reaction equation
Brc1ccc2ncccc2c1.Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O>CC(=O)[O-].CC(=O)[O-].CN(C)C=O.O=C([O-])[O-].[CH]1[CH][CH]C(P(c2ccccc2)c2ccccc2)[CH]1.[CH]1[CH][CH]C(P(c2ccccc2)c2ccccc2)[CH]1.[Cs+].[Cs+].[Fe].[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 1.781%HCID 792436-BromoquinolineYield 62.325%HCID 6207116,6'-BiquinolineYield 0%HCID 10751213HCID 10751213, compoundYield 2.451%HCID 129009568[5-Methyl-1-(oxan-2-yl)-1H-indazol-4-yl]boronic acidYield 21.831%HCID 178422846HCID 178422846, compoundYield 11.612%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 167845palladium(II) acetateCatalystHCID 178477755HCID 178477755, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Sources & evidence

ORD record
ord-39a3beeabd7143d0b6143b42d509f62e
Source dataset
HTE Suzuki coupling dataset

Reaction notes

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