6-Bromoquinoline → 6-Bromoquinoline

HRID 2259075Notes

Reaction equation

HRID 2259075 reaction equation
Brc1ccc2ncccc2c1.Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O>CC(=O)[O-].CC(=O)[O-].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CN(C)C=O.[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 3.248%HCID 792436-BromoquinolineYield 57.964%HCID 6207116,6'-BiquinolineYield 9.422%HCID 10751213HCID 10751213, compoundYield 2.104%HCID 129009568[5-Methyl-1-(oxan-2-yl)-1H-indazol-4-yl]boronic acidYield 27.262%HCID 178422846HCID 178422846, compoundYield 0%

Reagents, catalysts & solvents 4

HCID 25953Cesium fluorideReagentHCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Sources & evidence

ORD record
ord-706a026692364b5c9e54ba03ec8e3bc3
Source dataset
HTE Suzuki coupling dataset

Reaction notes

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