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Triphenylphosphine Oxide → 5-chloro-N-[2-(4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]thiophene-2-sulfonamide

HRID 1851451
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1851451
C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[Cl:36][C:37]1[S:41][C:40]([S:42]([NH:45][C:46]2[CH:47]=[CH:48][CH:49]=[C:50]3[C:54]=2[NH:53][C:52]([C:55]([NH:57][CH2:58][CH2:59][S:60]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=O)=[CH:51]3)(=[O:44])=[O:43])=[CH:39][CH:38]=1>ClCCl>[Cl:36][C:37]1[S:41][C:40]([S:42]([NH:45][C:46]2[CH:47]=[CH:48][CH:49]=[C:50]3[C:54]=2[NH:53][C:52]([C:55]2[S:60][CH2:59][CH2:58][N:57]=2)=[CH:51]3)(=[O:44])=[O:43])=[CH:39][CH:38]=1
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Komponenten

5

Edukt 3

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 579017477-{[(5-Chloro-2-thienyl)sulfonyl]amino}-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide

Produkt 1

HCID 579016245-chloro-N-[2-(4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]thiophene-2-sulfonamideAusbeute 37,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a solution of triphenylphosphine oxide (3.57 g) in dichloromethane (20 mL) was slowly added trifluoromethanesulfonic anhydride (1.10 mL) at 0° C. The mixture was stirred for 10 min, and 7-{[(5-chloro-2-thienyl)sulfonyl]amino}-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide (1.41 g) was added. The reaction mixture was stirred at room temperature for 3 hr and concentrated. Saturated aqueous sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography and the title compound (0.32 g, yield 37%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:20→1:1, volume ratio). melting point>210° C. (decomposition).

Aufarbeitung

  1. customat 0° C
  2. stirringThe reaction mixture was stirred at room temperature for 3 hr
  3. concentrationconcentrated
  4. additionSaturated aqueous sodium hydrogen carbonate was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-faa7e714956c4eecb2a05f8bd8ec325b
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08957070B2

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