4-((5-Fluoropyridin-2-yl)methoxy)pyridin-2(1H)-one → 8-(4-((5-Fluoropyridin-2-yl)methoxy)-2-oxopyridin-1(2H)-yl)-6-methyl-2,3,4,5-tetrahydroazepino[4,3-b]indol-1(6H)-one

HRID 475008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475008
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:16](=[O:17])[NH:15][CH2:14][CH2:13][CH2:12][C:7]=3[N:8]([CH3:11])[C:9]=2[CH:10]=1.[F:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][O:26][C:27]2[CH:32]=[CH:31][NH:30][C:29](=[O:33])[CH:28]=2)=[N:23][CH:24]=1>>[F:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][O:26][C:27]2[CH:32]=[CH:31][N:30]([C:2]3[CH:3]=[CH:4][C:5]4[C:6]5[C:16](=[O:17])[NH:15][CH2:14][CH2:13][CH2:12][C:7]=5[N:8]([CH3:11])[C:9]=4[CH:10]=3)[C:29](=[O:33])[CH:28]=2)=[N:23][CH:24]=1

Komponenten

3

Edukt 2

HCID 579503414-((5-Fluoropyridin-2-yl)methoxy)pyridin-2(1H)-oneHCID 668730848-bromo-6-methyl-2,3,4,5-tetrahydroazepino[4,3-b]indol-1(6H)-one

Produkt 1

HCID 498700518-(4-((5-Fluoropyridin-2-yl)methoxy)-2-oxopyridin-1(2H)-yl)-6-methyl-2,3,4,5-tetrahydroazepino[4,3-b]indol-1(6H)-oneAusbeute 21,8 %

Versuchsvorschrift

8-Bromo-6-methyl-2,3,4,5-tetrahydroazepino[4,3-b]indol-1(6H)-one (100 mg, 0.340 mmol) and 4-((5-fluoropyridin-2-yl)methoxy)pyridin-2(1H)-one (102 mg, 0.510 mmol) were reacted following the procedure for Example 2 (step d) to provide the title compound (32 mg, 21%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 8.53 (d, J=8.6 Hz, 1H), 8.48 (s, 1H), 7.51-7.46 (m, 2H), 7.37-7.31 (m, 2H), 7.13-7.17 (dd, J=8.5, 1.8 Hz, 1H), 6.12-6.03 (m, 2H), 5.93-5.86 (m, 1H), 5.17 (s, 2H), 3.66 (s, 3H), 3.42-3.34 (m, 2H), 3.09 (t, J=6.8 Hz, 2H), 2.28-2.19 (m, 2H); ESI MS m/z 433 [M+H]+; HPLC (Method B) 98.7% (AUC), tR=13.8 min.

Quellen und Nachweise

ORD-Eintrag
ord-f5ccd98a38f144bc947a288f34f6be88
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637501B2

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