2-(Tributylstannyl)furan → HCID 71268210, Verbindung

HRID 926432Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 926432
C([Sn](CCCC)(CCCC)[C:6]1[O: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[O: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 43936882-(Tributylstannyl)furanHCID 67428497HCID 67428497, Verbindung

Produkt 1

HCID 71268210HCID 71268210, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(Tributylstannyl)furan (472 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-(furan-2-yl)-2-nitropyrrole (111 mg, 0.38 mmol, 76%).

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-d3caa3adac6b4109bea4f5b569c69ba7
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09285319B2

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