2-(Methylthio)benzeneboronic acid → 9-hydroxy-4-[2-(methylsulfanyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11032

Reaktionsgleichung

Reaktionsgleichung von HRID 11032
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=[C:8](I)[C:7]4[C:16](=[O:20])[NH:17][C:18](=[O:19])[C:6]=4[C:5]=3[C:4]=2[CH:3]=1.[CH3:21][S:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O.CO.C(Cl)Cl>CCCCCC>[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=[C:8]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[S:22][CH3:21])[C:7]4[C:16](=[O:20])[NH:17][C:18](=[O:19])[C:6]=4[C:5]=3[C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 27735432-(Methylthio)benzeneboronic acidHCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneHCID 21226129Dichloromethane methanol

Produkt 1

HCID 99766729-hydroxy-4-[2-(methylsulfanyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 2-(methylthio)benzeneboronic acid according to the procedure described in example 8 gave 9-hydroxy-4-[2-(methylsulfanyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (508) (I; Ar=2-(methylsulfanyl)phenyl) in a 72% yield, mp (MeOH/CH2Cl2)/hexane) 208–216° C. 1H NMR [(CD3)2SO] δ 11.76 (br s, 1H), 10.95 (br s, 1H), 9.25 (br s, 1H), 8.31 (d, J=2.5 Hz, 1H), 7.47 (s, 1H), 7.44 (d, J=8.6 Hz, 1H), 7.43 (td, J=7.3, 2.2 Hz, 1H), 7.38 (br d, J=7.5 Hz, 1H), 7.27 (dd, J=7.8, 2.2 Hz, 1H), 7.24 (td, J=7.3, 1.3 Hz, 1H), 7.07 (dd, J=8.7, 2.5 Hz, 1H), 2.32 (s, 3H). Found: C, 66.55; H, 3.88; N, 7.38. C21H14N2O3S.1/4H2O requires C, 66.57; H, 3.86; N, 7.39.

Quellen und Nachweise

ORD-Eintrag
ord-98f64418f5764e489d7aefe7baf82a82
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094798B1

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