Water → HCID 11501404, compound

HRID 598094Notes

Reaction equation

HRID 598094 reaction equation
Br[C:2]1[N:3]([CH:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])[C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[C:8]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=1[CH3:20])[CH:7]=[CH:6][CH:5]=2.[CH3:28]B(O)O.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.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>[CH3:20][C:14]1[CH:15]=[C:16]([CH3:19])[CH:17]=[CH:18][C:13]=1[C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[C:10](=[O:12])[C:11]([CH3:28])=[CH:2][N:3]2[CH:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 67267023HCID 67267023, compound

Product 1

HCID 11501404HCID 11501404, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

3 Bromo-5-(2,4-dimethylphenyl)-1-(1-propylbutyl)quinolin-4(1H)-one was then charged with methylboronic acid (0.19 g, 3.2 mmol), potassium carbonate (0.22 g, 1.6 mmol), tetrakis(triphenylphosphine)palladium(0) (0.18 g, 0.16 mmol) and diluted with dioxane (8 mL) under nitrogen gas. Water (29 μL, 1.6 mmol) was added last. The reaction was stirred at 90° C. overnight. The solution was cooled and concentrated. Flash chromatography (40% ethyl acetate/hexanes) gave 0.049 g (43% yield) of the title compound as a white solid.

Workup

  1. temperatureThe solution was cooled
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a8f5998599cf442cb917fd509e56fb0d
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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