6-Bromoquinoline → 6-Bromoquinoline

HRID 2259019Notes

Reaction equation

HRID 2259019 reaction equation
Brc1ccc2ncccc2c1.Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O>C1CCOC1.CC(=O)[O-].CC(=O)[O-].CCCCP([C@]12C[C@H]3C[C@H](C[C@H](C3)C1)C2)[C@]12C[C@H]3C[C@H](C[C@H](C3)C1)C2.[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 2.702%HCID 792436-BromoquinolineYield 69.848%HCID 6207116,6'-BiquinolineYield 0%HCID 10751213HCID 10751213, compoundYield 1.942%HCID 129009568[5-Methyl-1-(oxan-2-yl)-1H-indazol-4-yl]boronic acidYield 25.508%HCID 178422846HCID 178422846, compoundYield 0%

Reagents, catalysts & solvents 4

HCID 25953Cesium fluorideReagentHCID 167845palladium(II) acetateCatalystHCID 178454859HCID 178454859, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Sources & evidence

ORD record
ord-4ac4f076ae3b43a78119fc1177663904
Source dataset
HTE Suzuki coupling dataset

Reaction notes

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