Sodium Carbonate → HCID 86671496, Verbindung

HRID 536627

Reaktionsgleichung

Reaktionsgleichung von HRID 536627
Br[C:2]1[C:6]([Br:7])=[CH:5][S:4][C:3]=1[CH:8]=[O:9].[CH3:10][C:11]1[CH:12]=[C:13]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:14]=[CH:15][C:16]=1B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O>[Br:7][C:6]1[C:2]([C:16]2[CH:15]=[CH:14][C:13]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])=[CH:12][C:11]=2[CH3:10])=[C:3]([CH:8]=[O:9])[S:4][CH:5]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 125595283,4-Dibromothiophene-2-carbaldehydeHCID 66715578HCID 66715578, Verbindung

Produkt 1

HCID 86671496HCID 86671496, VerbindungAusbeute 323,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To the solution of Intermediate 1 (4 g, 15 mmol) in a mixture of DME and H2O (150 mL/50 mL) were added N-(3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (3.6 g, 1.65 mmol) and Na2CO3 (2.8 g, 3.1 mmol), the mixture was degassed with N2, and Pd(PPh3)4 (500 mg) was added, then the mixture was heated to 100° C. under N2 overnight. The reaction solution was concentrated to remove the organic solution, then the aqueous layer was extracted with EtOAc (100 mL×3). The combined organic layers were washed with brine, dried over Na2SO4, concentrated under reduced pressure, the residue was purified by column chromatography to give N-(4-(4-bromo-2-formylthiophen-3-yl)-3-methylphenyl)methanesulfonamide (2.0 g, yield 35.7%).

Aufarbeitung

  1. customthe mixture was degassed with N2, and Pd(PPh3)4 (500 mg)
  2. additionwas added
  3. concentrationThe reaction solution was concentrated
  4. customto remove the organic solution
  5. extractionthe aqueous layer was extracted with EtOAc (100 mL×3)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1494e7372e5247a1b3caa74ff144e352
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859611B2

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