Cesium carbonate → HCID 58938600, compound

HRID 598179Notes

Reaction equation

HRID 598179 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[C:13](Br)[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:19])[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[C:22]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([C:22]3[C:23]([CH3:28])=[CH:24][C:25]([CH3:27])=[CH:26][C:21]=3[CH3:20])[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:19])[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2921842,4,6-Trimethylbenzeneboronic acidHCID 67267657HCID 67267657, compound

Product 1

HCID 58938600HCID 58938600, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

1-Benzyl-5-bromoquinolin-4(1H)-one (1.52 g, 4.84 mmol), 2,4,6-trimethylphenylboronic acid (1.19 g, 7.26 mmol), 2,8,9-trisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (0.331 g, 0.97 mmol), Pd(OAc)2 (0.11 g, 0.48 mmol), and cesium carbonate (3.15 g, 9.68 mmol) were diluted in 25 mL of toluene and stirred for 3 hr. at 80° C. The solution was cooled and concentrated. Flash chromatography of the residue (50-75% Ethyl acetate/hexanes) gave the title compound as a white solid (0.52 g, 30%).

Workup

  1. customat 80° C
  2. temperatureThe solution was cooled
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9010b804e7e7416f922a76911ca76e8e
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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