Potassium Carbonate → HCID 25168520, compound

HRID 561039Notes

Reaction equation

HRID 561039 reaction equation
Cl[C:2]1(O)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13].[Cl:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][C:3]=2[S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 67000483HCID 67000483, compound

Product 1

HCID 25168520HCID 25168520, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-chloro-3-(4-methyl-benzenesulfonyl)-quinolin-4-ol (0.2 g, 0.67 mmol) and 4-chlorophenylboronic acid (0.16 g, 1.0 mmol) in 8 ml dioxane was stirred for 20 hours at 90° C. with potassium carbonate (0.5 g, 3.6 mmol) and tetrakis-(triphenylphosphin)palladium(0) (0.04 g, 0.035 mmol). After cooling the mixture was concentrated in vacuo. The crude residue was purified by column chromatography on silica gel (Kieselgel 60, eluent: chloroform) to obtain 0.21 g of the title compound in 80% yield.

Workup

  1. temperatureAfter cooling the mixture
  2. concentrationwas concentrated in vacuo
  3. customThe crude residue was purified by column chromatography on silica gel (Kieselgel 60, eluent: chloroform)

Sources & evidence

ORD record
ord-a1646a254bf445c5b71450bb92fc1632
Source dataset
uspto-grants-2011_11
Patent number
US08063220B2

Reaction notes

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