Potassium Phosphate, Tribasic → 5-(2,4-Dimethylphenyl)-4-oxo-1-(1-propylbutyl)-1,4-dihydroquinoline-3-carbonitrile

HRID 598178Notes

Reaction equation

HRID 598178 reaction equation
Cl[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:19]#[N:20])=[CH:6][N:7]2[CH:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15].[CH3:22][C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:22][C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=1[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:19]#[N:20])=[CH:6][N:7]2[CH:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 4198739(2,4-Dimethylphenyl)boronic acidHCID 672675855-Choro-4-oxo-1-(1-propylbutyl)-1,4-dihydroquinoline-3-carbonitrile

Product 1

HCID 672674715-(2,4-Dimethylphenyl)-4-oxo-1-(1-propylbutyl)-1,4-dihydroquinoline-3-carbonitrileYield 50%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

5-Choro-4-oxo-1-(1-propylbutyl)-1,4-dihydroquinoline-3-carbonitrile (0.015 g, 0.05 mmol), 2,4-dimethylbenzeneboronic acid (0.012 g, 0.079 mmol), and PdCl2(PPh3)2 (0.010 g, 0.015 mmol) were suspended in toluene (1 mL). K3PO4 (0.074 mL, 0.15 mmol, 2M in water) was added last. The reaction was stirred at 90° C. with stirring overnight. The mixture was cooled, filtered through GF/F paper and concentrated. Flash chromatography (40% Ethyl acetate/hexanes) gave the desired product (0.009 g, 50%).

Workup

  1. stirringwith stirring overnight
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through GF/F paper
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9758af6671fc420593be7b4698c78c0b
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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