4-(4-Chlorophenyl)-2-hydroxypyridine → 4-(4-Chlorophenyl)-1-(2,9-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-7-yl)pyridin-2(1H)-one hydrochloride

HRID 930651Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 930651
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1.Br[C:16]1[CH:24]=[C:23]2[C:19]([C:20]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][C:21]=3[N:22]2[CH3:25])=[CH:18][CH:17]=1>>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]([C:16]3[CH:24]=[C:23]4[C:19]([C:20]5[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][C:21]=5[N:22]4[CH3:25])=[CH:18][CH:17]=3)[C:10](=[O:14])[CH:9]=2)=[CH:6][CH:7]=1

Komponenten

3

Edukt 2

HCID 189872944-(4-Chlorophenyl)-2-hydroxypyridineHCID 579503597-Bromo-2,9-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Produkt 1

HCID 686574654-(4-Chlorophenyl)-1-(2,9-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-7-yl)pyridin-2(1H)-one hydrochlorideAusbeute 38,5 %

Versuchsvorschrift

4-(4-Chlorophenyl)pyridin-2(1H)-one (80 mg, 0.33 mmol) and 7-bromo-2,9-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (49 mg, 0.33 mmol) were reacted following the procedure of Example 30 (step g) to provide the title compound (28 mg, 19%) as a yellow-green solid: mp 316-323° C.; 1H NMR (500 MHz, DMSO-d6) δ 11.0 (br s, 1H), 7.83 (dd, J=6.8, 1.9 Hz, 2H), 7.76 (d, J=7.1 Hz, 1H), 7.62-7.57 (m, 4H), 7.07 (dd, J=8.3, 1.8 Hz, 1H), 6.81 (d, J=2.0 Hz, 1H), 6.69 (dd, J=7.2, 2.1 Hz, 1H), 4.79 (d, J=15.2 Hz, 1H), 4.44 (dd, J=15.2, 6.0 Hz, 1H), 3.74-3.68 (m, 4H), 3.48-3.38 (m, 1H), 3.10-2.99 (m, 5H); ESI MS m/z 404 [M+H]+; HPLC (Method B)>99% (AUC), tR=13.5 min.

Quellen und Nachweise

ORD-Eintrag
ord-0fa4423b6d444cfba9a409562af69c8f
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296743B2

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