6-Bromoquinoline → 6-Bromoquinoline

HRID 2258963Notes

Reaction equation

HRID 2258963 reaction equation
Brc1ccc2ncccc2c1.Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O>CC#N.CC(=O)[O-].CC(=O)[O-].CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.[Cs+].[F-].[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 0.764%HCID 792436-BromoquinolineYield 70.758%HCID 6207116,6'-BiquinolineYield 0%HCID 10751213HCID 10751213, compoundYield 3.254%HCID 129009568[5-Methyl-1-(oxan-2-yl)-1H-indazol-4-yl]boronic acidYield 25.224%HCID 178422846HCID 178422846, compoundYield 0%

Reagents, catalysts & solvents 4

HCID 25953Cesium fluorideReagentHCID 167845palladium(II) acetateCatalystHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Sources & evidence

ORD record
ord-b3d8f3f5ae6642da9a1990eb10a8d863
Source dataset
HTE Suzuki coupling dataset

Reaction notes

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