Sodium Carbonate → HCID 58828884, Verbindung

HRID 908323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 908323
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=[CH:12]3)O1.Br[C:25]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:26]=1[CH:27]=[CH:28][N:29]=[CH:30]2.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.CCO>[CH:30]1[C:31]2[C:26](=[C:25]([C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][CH:18]=3)[C:15]([C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=[CH:12]4)[CH:34]=[CH:33][CH:32]=2)[CH:27]=[CH:28][N:29]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 7364875-BromoisoquinolineHCID 58828895Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-carboxylate

Produkt 1

HCID 58828884HCID 58828884, VerbindungAusbeute 70,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21863594Toluene ethanolLösungsmittel

Versuchsvorschrift

Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthoate (2.2 g, 7.0 mmol), 5-Bromoisoquinoline (1.33 g, 6.3 mmol), a 2M solution of sodium carbonate (9.6 mL) and palladium tetrakistriphenylphospine (0.37 g, 0.32 mmol) were heated in Toluene-EtOH (105 mL-21 mL) at 80° C. overnight. Solvent was evaporated and mixture was extracted with ethyl acetate. Organic phase was washed with brine, dried, filtered and evaporated. Residue was purified by chromatography (ethyl acetate-hexane 10:90->20:80->30:70->40:60->60-40. to give 1.4 g of the title compound as an off-white solid

Aufarbeitung

  1. customSolvent was evaporated
  2. extractionmixture was extracted with ethyl acetate
  3. washOrganic phase was washed with brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customResidue was purified by chromatography (ethyl acetate-hexane 10:90->20:80->30:70->40:60->60-40

Quellen und Nachweise

ORD-Eintrag
ord-254d9feadf6c42949d969310108d3413
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017601B2

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