Tributylvinyltin → 9-Benzenesulfonyl-5-vinyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 1888506Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1888506
[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:27]#[N:28])=[C:18](OS(C(F)(F)F)(=O)=O)[C:13]=3[C:12]3[CH:29]=[CH:30][CH:31]=[N:32][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:33]([Sn](CCCC)(CCCC)C=C)[CH2:34]CC.[Cl-].[Li+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:27]#[N:28])=[C:18]([CH:33]=[CH2:34])[C:13]=3[C:12]3[CH:29]=[CH:30][CH:31]=[N:32][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 58266643HCID 58266643, Verbindung

Produkt 1

HCID 582665259-Benzenesulfonyl-5-vinyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrileAusbeute 53,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of trifluoromethanesulfonic acid 9-benzenesulfonyl-6-cyano-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-5-yl ester (150 mg, 0.31 mmol), tributyl(vinyl)stannane (102 μL, 0.35 mmol), lithium chloride (40 mg, 0.93 mmol) and tetrakis(triphenylphosphine)palladium(0) (7.0 mg, 6.0 μmol) in dioxane (1.5 mL) was degassed with argon and heated under reflux for 18 h. The reaction mixture was allowed to cool to ambient temperature then diluted with DCM (9 mL) and methanol (1 mL). The resultant residue was purified by chromatography (silica, 2 g column, Si-SPE, 0-2% MeOH in DCM) and triturated with pentane (2×2 mL) to afford the title compound as a white solid (60 mg, 52%). LCMS (Method B): RT=3.73 min, M+H+=361.

Aufarbeitung

  1. customwas degassed with argon
  2. temperatureheated
  3. temperatureunder reflux for 18 h
  4. additionthen diluted with DCM (9 mL) and methanol (1 mL)
  5. customThe resultant residue was purified by chromatography (silica, 2 g column, Si-SPE, 0-2% MeOH in DCM)
  6. customtriturated with pentane (2×2 mL)

Quellen und Nachweise

ORD-Eintrag
ord-1690dfa08cae43748e2bd8271985576f
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501765B2

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