Sodium Carbonate → 5-(3,5-Dimethoxy-phenyl)-quinoline-8-carboxylic acid

HRID 43192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 43192
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.Br[C:15]1[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[N:20]2.C([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+]>CCO.C1(C)C=CC=CC=1.CCOC(C)=O.O.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]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[C:21]3[C:16]=2[CH:17]=[CH:18][CH:19]=[N:20]3)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Komponenten

10

Edukt 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 4374257(3,5-Dimethoxyphenyl)boronic acidHCID 592928605-Bromoquinoline-8-carboxylic acid

Produkt 1

HCID 592928765-(3,5-Dimethoxy-phenyl)-quinoline-8-carboxylic acidAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A mixture of 3,5-dimethoxyphenylboronic acid (217 mg, 1.19 mmol, 1.2 equiv) (Step 1.8) in EtOH (0.5 mL) was added dropwise to a mixture of 5-bromo-quinoline-8-carboxylic acid (Step 159.3) (250 mg, 0.99 mmol), PdCl2(dppf) (22 mg, 0.03 mmol, 0.03 equiv), Na2CO3 (2M solution in H2O, 1 mL, 3.97 mmol, 4 equiv) in toluene (5 mL) at 105° C., under an argon atmosphere. The reaction mixture was stirred at 105° C. for 1 h, allowed to cool to rt, diluted with EtOAc and H2O, basified by addition of a 2N aqueous solution of NaOH (2 mL), filtered through a pad of celite and the filtrate was extracted with EtOAc. The aqueous layer was separated and acidified to pH 5. The resulting precipitate was collected by vacuum filtration to provide 248 mg of the title compound as a white solid: ESI-MS: 310.1 [M+H]+; tR=4.06 min (System 1).

Aufarbeitung

  1. temperatureto cool to rt
  2. filtrationfiltered through a pad of celite
  3. extractionthe filtrate was extracted with EtOAc
  4. customThe aqueous layer was separated
  5. filtrationThe resulting precipitate was collected by vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-3bf40791a5b34a20b2709d8368665a72
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536175B2

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