5-Fluoro-2-methylphenylboronic acid → 4-amino-8-(5-fluoro-2-methyl-phenyl)-N-propyl-cinnoline-3-carboxamide

HRID 31103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 31103
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](Br)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH2:17][CH3:18])=[O:14].[F:19][C:20]1[CH:21]=[CH:22][C:23]([CH3:29])=[C:24](B(O)O)[CH:25]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:22]3[CH:21]=[C:20]([F:19])[CH:25]=[CH:24][C:23]=3[CH3:29])[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH2:17][CH3:18])=[O:14]

Komponenten

3

Edukt 2

HCID 27831905-Fluoro-2-methylphenylboronic acidHCID 140123264-Amino-8-bromo-N-propylcinnoline-3-carboxamide

Produkt 1

HCID 251324334-amino-8-(5-fluoro-2-methyl-phenyl)-N-propyl-cinnoline-3-carboxamideAusbeute 86,5 %

Versuchsvorschrift

Using method A, 4-amino-8-bromo-N-propyl-cinnoline-3-carboxamide (150 mg, 0.485 mmol) and 5-fluoro-2-methyl-phenylboronic acid (154 mg, 1.000 mmol) were reacted to afford the title compound (142 mg, 86% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.53 (br, 1H), 7.91 (m, 1H), 7.77-7.63 (m, 2H), 7.26 (m, 1H), 7.07-6.97 (m, 2H), 3.45 (apparent quartet, J=7.0 Hz, 2H), 2.01 (s, 3H), 1.65 (apparent sextet, J=7.0 Hz, 2H), 0.99 (t, J=7.0 Hz, 3H). MS APCI, m/z=339 (M+H). HPLC 1.77 min.

Aufarbeitung

  1. customwere reacted

Quellen und Nachweise

ORD-Eintrag
ord-b4150e4a614d4d5e86e82b85857a4d72
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425556B2

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