6-Bromoquinoline → HCID 178422846, compound

HRID 2258795Notes

Reaction equation

HRID 2258795 reaction equation
Brc1ccc2ncccc2c1.Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O>CC(=O)[O-].CC(=O)[O-].CO.[Cs+].[F-].[Pd+2].c1ccc(P(c2ccccc2)c2ccccc2)cc1>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 3.004%HCID 792436-BromoquinolineYield 15.965%HCID 6207116,6'-BiquinolineYield 3.599%HCID 10751213HCID 10751213, compoundYield 2.457%HCID 129009568[5-Methyl-1-(oxan-2-yl)-1H-indazol-4-yl]boronic acidYield 0.132%HCID 178422846HCID 178422846, compoundYield 74.222%

Reagents, catalysts & solvents 4

HCID 25953Cesium fluorideReagentHCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Sources & evidence

ORD record
ord-c895f7a570b44c3494364059a982370d
Source dataset
HTE Suzuki coupling dataset

Reaction notes

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