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6-Bromoquinoline → 6-Bromoquinoline

HRID 2258785
Notes
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Reaction equation

HRID 2258785 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.CO.[Na+].[OH-].[Pd+2]>Cc1ccc2c(cnn2C2CCCCO2)c1.Cc1ccc2c(cnn2C2CCCCO2)c1-c1ccc2ncccc2c1.c1ccc2ncccc2c1.c1cnc2ccc(-c3ccc4ncccc4c3)cc2c1
ParticipantsConditionsSources & evidenceReaction notes

Participants

12

Reactant 2

HCID 792436-BromoquinolineHCID 129009568[5-Methyl-1-(oxan-2-yl)-1H-indazol-4-yl]boronic acid

Product 6

HCID 7047QuinolineYield 4.168%HCID 792436-BromoquinolineYield 42.424%HCID 6207116,6'-BiquinolineYield 6.416%HCID 10751213HCID 10751213, compoundYield 2.392%HCID 129009568[5-Methyl-1-(oxan-2-yl)-1H-indazol-4-yl]boronic acidYield 18.03%HCID 178422846HCID 178422846, compoundYield 26.572%

Reagents, catalysts & solvents 4

HCID 14798Sodium HydroxideReagentHCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Sources & evidence

ORD record
ord-17e0d2f5e0f74104b5de312655b5f72c
Source dataset
HTE Suzuki coupling dataset
DOI
10.1021/jacs.2c08592

Reaction notes

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On this pageParticipantsConditionsSources & evidenceReaction notes