2-(Tri-n-butylstannyl)thiophene → HCID 71268199, Verbindung

HRID 926431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 926431
C([Sn](CCCC)(CCCC)[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)CCC.[C@@H:19]1([N:27]2[CH:31]=[C:30](I)[CH:29]=[C:28]2[N+:33]([O-:35])=[O:34])[O:24][C@H:23]([CH2:25][OH:26])[C@@H:21]([OH:22])[CH2:20]1>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.CN(C=O)C>[C@@H:19]1([N:27]2[CH:31]=[C:30]([C:6]3[S:7][CH:8]=[CH:9][CH:10]=3)[CH:29]=[C:28]2[N+:33]([O-:35])=[O:34])[O:24][C@H:23]([CH2:25][OH:26])[C@@H:21]([OH:22])[CH2:20]1

Komponenten

5

Edukt 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 67428497HCID 67428497, Verbindung

Produkt 1

HCID 71268199HCID 71268199, VerbindungAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(Tributylstannyl)thiophene (476 μL, 1.5 mmol) was added to a DMF (2.5 mL) solution containing 1-(2-deoxy-β-D-ribofuranosyl)-4-iodo-2-nitropyrrole (177 mg, 0.5 mmol) and bis(triphenylphosphine)palladium(II) dichloride (18 mg, 0.025 mmol). The mixture was reacted at 100° C. for 30 minutes in a microwave machine (standard mode). The reaction solution was separated between ethyl acetate (50 mL) and water (50 mL). The organic layer was concentrated and purified by HPLC to yield 1-(2-deoxy-β-D-ribofuranosyl)-4-(thien-2-yl)-2-nitropyrrole (97 mg, 0.32 mmol, 63%).

Aufarbeitung

  1. customThe mixture was reacted at 100° C. for 30 minutes in a microwave machine (standard mode)
  2. customThe reaction solution was separated between ethyl acetate (50 mL) and water (50 mL)
  3. concentrationThe organic layer was concentrated
  4. custompurified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-6ba9b98c7dec42908d326081d6b00494
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09285319B2

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