Dichloromethane → 2-(4-Nitrophenyl)-4-quinolinecarboxylic acid methyl ester

HRID 1259861

반응식

HRID 1259861 반응식
C(Cl)Cl.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[N+:12]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)([O-:14])=[O:13].[CH3:24][O:25][C:26]([C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=[C:30](Cl)[CH:29]=1)=[O:27]>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>[CH3:24][O:25][C:26]([C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=[C:30]([C:18]2[CH:19]=[CH:20][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=2)[CH:29]=1)=[O:27]

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 27735524-Nitrophenylboronic acidHCID 5202936Methyl 2-chloroquinoline-4-carboxylate

생성물 1

HCID 34203702-(4-Nitrophenyl)-4-quinolinecarboxylic acid methyl ester수율 78.8%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 6228Dimethylformamide용매HCID 312751,4-Dioxane용매

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온도
85 °C

실험 절차

PdCl2(dppf).CH2Cl2 (184 mg, 0.23 mmol), tripotassium phosphate (624 mg, 4.51 mmol), and 4-nitrophenylboronic acid (958 mg, 4.51 mmol) were added to a 1,4-dioxane (5 mL)/DMF (1 mL) mixed solution of 2-chloro-4-quinolinecarboxylic acid methyl ester (500 mg, 2.26 mmol) obtained in Reference Example 3, and the mixture was heated with stirring overnight at 85° C. 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-nitrophenyl)-4-quinolinecarboxylic acid methyl ester (549 mg, 1.78 mmol).

후처리

  1. customobtained in Reference Example 3
  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

출처 및 근거

ORD 기록
ord-eee545d12a32431c9e711717562ac72d
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466290B2

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