Sodium Carbonate → HCID 118574956, Verbindung

HRID 632670

Reaktionsgleichung

Reaktionsgleichung von HRID 632670
Br[C:2]1[S:6][C:5]2[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:4]=2[C:3]=1[O:13][C:14]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=1.[CH3:26][O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>COCCOC.CCOC(C)=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]>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:4]2[C:3]([O:13][C:14]3[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=3)=[C:2]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[CH2:28][O:27][CH3:26])[S:6][C:5]=2[CH:7]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 37594082-(Methoxymethyl)benzeneboronic acidHCID 118574969(E)-methyl 3-(4-((2-bromo-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate

Produkt 1

HCID 118574956HCID 118574956, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (E)-methyl 3-(4-((2-bromo-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate (100 mg, 0.238 mmol) in 1,2-dimethoxyethane (3.0 mL) was added (2-(methoxymethyl)phenyl)boronic acid (79 mg, 0.477 mmol). [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (17.5 mg, 0.024 mmol) and Na2CO3 (2.0N aqueous, 0.358 mL, 0.715 mmol). The resulting mixture was subjected to microwave irradiation at 100° C. for 20 min after which time the reaction was diluted with EtOAc, added anhydrous Na2SO4, filtered and concentrated in vacuo. The crude material was purified by column chromatography (SiO2, 0-20% EtOAc/Heptane) to afford (E)-methyl 3-(4-((6-methoxy-2-(2-(methoxymethyl)phenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylate (86.6 mg, 0.188 mmol, 79% yield). LC/MS (m/z, M+H2O): 478.0.

Aufarbeitung

  1. customirradiation at 100° C. for 20 min after which time the reaction
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by column chromatography (SiO2, 0-20% EtOAc/Heptane)

Quellen und Nachweise

ORD-Eintrag
ord-364a5e55c79f427b80549f529f15f9e7
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321746B2

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