Dichloromethane → HCID 67204410, compound

HRID 1259862Notes

Reaction equation

HRID 1259862 reaction equation
C(Cl)Cl.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:12]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)(=[O:14])[CH3:13].[CH2:24]([O:31][C:32]([C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[N:37]=[C:36](Cl)[CH:35]=1)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CN(C=O)C.O1CCOCC1>[CH2:24]([O:31][C:32]([C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[N:37]=[C:36]([C:18]2[CH:19]=[CH:20][C:15]([C:12](=[O:14])[CH3:13])=[CH:16][CH:17]=2)[CH:35]=1)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 37021224-Acetylphenylboronic acidHCID 9009683HCID 9009683, compound

Product 1

HCID 67204410HCID 67204410, compoundYield 67.9%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

PdCl2(dppf).CH2Cl2 (138 mg, 0.17 mmol), tripotassium phosphate (715 mg, 3.37 mmol), and 4-acetylphenylboronic acid (414 mg, 2.52 mmol) were added to a 1,4-dioxane (5 mL)/DMF (1 mL) mixed solution of 2-chloro-4-quinolinecarboxylic acid benzyl ester (500 mg, 1.68 mmol) obtained in Reference Example 4, and the mixture was heated with stirring at 85° C. for 10 hours in an argon atmosphere. After the reaction solution was concentrated, to the residue, a saturated aqueous solution of sodium chloride and methylene chloride were added, and insoluble matter was filtered off through celite. After that, the residue was subjected to extraction with methylene chloride and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography to obtain 2-(4-acetylphenyl)-4-quinolinecarboxylic acid benzyl ester (434 mg, 1.14 mmol).

Workup

  1. customobtained in Reference Example 4
  2. temperaturethe mixture was heated
  3. concentrationAfter the reaction solution was concentrated, to the residue
  4. additiona saturated aqueous solution of sodium chloride and methylene chloride were added
  5. filtrationinsoluble matter was filtered off through celite
  6. extractionAfter that, the residue was subjected to extraction with methylene chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9a0147d563554c68b5fbcdf47296556d
Source dataset
uspto-grants-2013_06
Patent number
US08466290B2

Reaction notes

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