Sodium Carbonate → HCID 22324115, Verbindung

HRID 496100Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 496100
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[C:4]([NH2:12])[CH:3]=1.C(B(CC)[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)C.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:12][C:4]1[CH:3]=[C:2]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:7]=[CH:6][C:5]=1[S:8]([NH2:11])(=[O:10])=[O:9]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 1245249554734-81-5

Produkt 1

HCID 22324115HCID 22324115, VerbindungAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of 4-bromo-2-aminobenzenesulfonamide (250 mg, 1.0 mmol), diethyl-3-pyridylborane (225 mg, 1.5 mmol), Pd(PPh3)2Cl2 (35 mg, 5 mol %) in 1,2-dimethoxyethane 30 ml) and Na2CO3 (2M, 3 ml, 6 mmol) were refluxed under N2 for 4 h. The solvents were removed under reduced pressure and the residue was treated with saturated NaHCO3 (20 ml) and extracted with EtOAc (2×40 ml). The organic layer was washed with brine (20 ml), dried (Na2SO4) and the solvent was removed under reduced pressure. The product was purified by flash chromatography on SiO2 using EtOAc:n-hexane (1:1, v/v) as eluent, yielding 240 mg (96%) of 2-amino-4-(3-pyridyl)-benzenesulfonamide as colorless powder. The product was further transformed by Method G (using cyclohexanecarboxaldehyde). M.p. 240-243° C.

Aufarbeitung

  1. temperaturewere refluxed under N2 for 4 h
  2. customThe solvents were removed under reduced pressure
  3. additionthe residue was treated with saturated NaHCO3 (20 ml)
  4. extractionextracted with EtOAc (2×40 ml)
  5. washThe organic layer was washed with brine (20 ml)
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was removed under reduced pressure
  8. customThe product was purified by flash chromatography on SiO2

Quellen und Nachweise

ORD-Eintrag
ord-090fe85ac1c5452db282e3fb674167eb
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06943159B1

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