Water → HCID 58938573, compound

HRID 598181Notes

Reaction equation

HRID 598181 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([C:18]3[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=3[CH3:26])[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:27])[C:10](Br)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29]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>[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([C:18]3[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=3[CH3:26])[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:27])[C:10]([CH3:29])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 58938574HCID 58938574, compound

Product 1

HCID 58938573HCID 58938573, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

1-Benzyl-3-bromo-5-mesitylquinolin-4(1H)-one (0.277 g, 0.64 mmol), methyl boronic acid (0.384 g, 6.4 mmol), potassium carbonate (0.443 g, 3.2 mmol), and Pd(PPh3)4 (0.37 g, 0.32 mmol) were diluted in dioxane (4 mL). Water (0.11 mL, 6.4 mmol) was added and the reaction stirred at 95° C. for 22 hr. The solution was then cooled and filtered through GF/F paper and concentrated. Flash chromatography (40% ethyl acetate/hexanes) gave the title compound as a white solid (0.14 g, 60%).

Workup

  1. temperatureThe solution was then cooled
  2. filtrationfiltered through GF/F paper
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-facdb59c84204568b001b7020c301461
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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