6-Bromoquinoline → 6-Bromoquinoline

HRID 2258934Notes

Reaction equation

HRID 2258934 reaction equation
Brc1ccc2ncccc2c1.Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O>CC#N.CC(=O)[O-].CC(=O)[O-].COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.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 1.304%HCID 792436-BromoquinolineYield 65.615%HCID 6207116,6'-BiquinolineYield 5.963%HCID 10751213HCID 10751213, compoundYield 2.733%HCID 129009568[5-Methyl-1-(oxan-2-yl)-1H-indazol-4-yl]boronic acidYield 23.794%HCID 178422846HCID 178422846, compoundYield 0.294%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 167845palladium(II) acetateCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Sources & evidence

ORD record
ord-359947d2f2444c44acf73b2db26e4dc1
Source dataset
HTE Suzuki coupling dataset

Reaction notes

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