2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → 9-hydroxy-4-(4-hydroxy-3-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11026Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 11026
[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][O:22][C:23]1[CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=[CH:25][C:24]=1[OH:38]>>[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=[C:8]([C:27]4[CH:26]=[CH:25][C:24]([OH:38])=[C:23]([O:22][CH3:21])[CH:28]=4)[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

3

Edukt 2

HCID 27346502-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Produkt 1

HCID 219807539-hydroxy-4-(4-hydroxy-3-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneAusbeute 58 %

Versuchsvorschrift

The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol according to the procedure described in example 8 gave 9-hydroxy-4-(4-hydroxy-3-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (23) (I, Ar=4-hydroxy-3-methoxyphenyl) in a 58% yield; mp 290–295° C. (dec). 1H NMR δ [(CD3)2SO] 11.67 (br s, 1H), 10.97 (br s, 1H), 9.22 (br s, 1H), 9.15 (s, 1H), 8.33 (d, J=2.4 Hz, 1H), 7.57 (s, 1H), 7.41 (d, J=8.6 Hz, 1H), 7.23 (d, J=2.0 Hz, 1H), 7.04 (m, 2H), 6.86 (d, J=8.1 Hz, 1H), 3.82 (s, 3H). FABMS found [M+H]+: 375.0973. C21H15N2O5 requires 375.0981.

Quellen und Nachweise

ORD-Eintrag
ord-1d65fb38e6e741e9922297145075bdcd
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094798B1

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