Cesium carbonate → HCID 178508699, Verbindung

HRID 527850Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527850
I[C:2]1[CH:10]=[CH:9][C:5]2[CH2:6][CH2:7][O:8][C:4]=2[CH:3]=1.[SH:11][C:12]1[NH:20][C:19]2[C:14](=[N:15][CH:16]=[N:17][C:18]=2[NH2:21])[N:13]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:8]1[C:4]2[CH:3]=[C:2]([S:11][C:12]3[NH:13][C:14]4[C:19]([N:20]=3)=[C:18]([NH2:21])[N:17]=[CH:16][N:15]=4)[CH:10]=[CH:9][C:5]=2[CH2:6][CH2:7]1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 671154566-Iodo-2,3-dihydrobenzofuranHCID 178508691HCID 178508691, Verbindung

Produkt 1

HCID 178508699HCID 178508699, VerbindungAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of S2-2 (50 mg, 0.2 mmol) in DMF (2 mL) was added 8-mercaptoadenine (34 mg, 0.2 mmol), Cs2CO3 (99.4 mg, 0.3 mmol) and PdCl2(dppf) (33 mg, 0.02 mmol). The mixture was degassed for 5 minutes with argon and stirred at 80° C. under argon protection for 48 h. The resulting mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (CH2Cl2:MeOH, 100:0 to 90:10) to provide S2-3 (25 mg, 44% yield) as a yellow solid.

Aufarbeitung

  1. customThe mixture was degassed for 5 minutes with argon
  2. concentrationThe resulting mixture was concentrated under reduced pressure
  3. customthe residue was purified by flash chromatography (CH2Cl2:MeOH, 100:0 to 90:10)
  4. customto provide S2-3 (25 mg, 44% yield) as a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-85c9be7c331e4c8a8e438662a053567f
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346808B2

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