Water → HCID 58938552, compound

HRID 598092Notes

Reaction equation

HRID 598092 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:19])[CH:5]=[CH:6][N:7]2[CH:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15].[CH3:20][C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:22]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].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.O1CCOCC1>[CH3:20][C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:22]=1[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:19])[CH:5]=[CH:6][N:7]2[CH:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 4198739(2,4-Dimethylphenyl)boronic acidHCID 67267021HCID 67267021, compound

Product 1

HCID 58938552HCID 58938552, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-Bromo-1-(1-propylbutyl)quinolin-4(1H)-one (0.096 g, 0.30 mmol), 2,4-dimethylbenzeneboronic acid (0.067 g, 0.45 mmol), potassium carbonate (0.124 g, 0.89 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.17 g, 0.15 mmol) were put under nitrogen gas. Dioxane (4 mL) was added followed by water (27 μL 1.5 mmol). The reaction was heated at 90° C. overnight. The solution was cooled and concentrated. Flash chromatography (60% ethyl acetate/hexanes) gave 0.088 g (85% yield) of the desired product.

Workup

  1. temperatureThe solution was cooled
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-eb513cb59e0e4fb7a6de3aa38de88634
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

Loading…