Water → 8-Phenylquinoline

HRID 1760099Notes

Reaction equation

HRID 1760099 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.O.C1N(COCCO)[C:16]2NC(N)=N[C:26](=O)[C:15]=2N=1.[C:29]([O-])([O-])=O.[K+].[K+].O1[CH2:40][CH2:39]OCC1>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:16]1([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)[CH:15]=[CH:26][CH:40]=[CH:39][CH:29]=1

Participants

8

Reactant 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 1401098-BromoquinolineHCID 178508935HCID 178508935, compound

Product 1

HCID 5219308-Phenylquinoline

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A degassed solution of 8-bromoquinoline (1.0 g, 4.81 mmol) (Aldrich) in dioxane (50 mL)/H2O (10 mL) was treated with phenylboronic acic (0.64 g, 5.29 mmol) (Aldrich), Pd(Ph3P)4 (0.050 g, 0.04 mmol) and K2CO3 (0.73 g, 5.29 mmol). After refluxing for 4 hours under a N2 atmosphere the reaction was allowed to cool, diluted with EtOAc and separated. After drying over Na2SO4 and SiO2 chromatography (95:5 Hexanes/EtOAc) the titled compound was isolated as a colorless oil.

Workup

  1. temperatureAfter refluxing for 4 hours under a N2 atmosphere the reaction
  2. temperatureto cool
  3. customseparated
  4. dry with materialAfter drying over Na2SO4 and SiO2 chromatography (95:5 Hexanes/EtOAc) the titled compound
  5. customwas isolated as a colorless oil

Sources & evidence

ORD record
ord-80698d92a163467495363d15c51fe8ec
Source dataset
uspto-grants-2005_01
Patent number
US06838455B2

Reaction notes

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