2-Bromo-3-fluorobenzonitrile → 6,2'-Difluoro-5'-[3-(1-hydroxy-1-methylethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]-4'-methoxybiphenyl-2-carbonitrile

HRID 891867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891867
[F:1][C:2]1[C:7](B2OC(C)(C)C(C)(C)O2)=[CH:6][C:5]([C:17]2[N:21]3[N:22]=[CH:23][C:24]([C:26]([OH:29])([CH3:28])[CH3:27])=[N:25][C:20]3=[N:19][CH:18]=2)=[C:4]([O:30][CH3:31])[CH:3]=1.Br[C:33]1[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:34]=1[C:35]#[N:36]>>[F:41][C:40]1[CH:39]=[CH:38][CH:37]=[C:34]([C:35]#[N:36])[C:33]=1[C:7]1[CH:6]=[C:5]([C:17]2[N:21]3[N:22]=[CH:23][C:24]([C:26]([OH:29])([CH3:27])[CH3:28])=[N:25][C:20]3=[N:19][CH:18]=2)[C:4]([O:30][CH3:31])=[CH:3][C:2]=1[F:1]

Komponenten

3

Edukt 2

HCID 27833932-Bromo-3-fluorobenzonitrileHCID 222400832-{7-[4-Fluoro-2-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]imidazo[1,2-b][1,2,4]triazin-3-yl}propan-2-ol

Produkt 1

HCID 222400846,2'-Difluoro-5'-[3-(1-hydroxy-1-methylethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]-4'-methoxybiphenyl-2-carbonitrileAusbeute 40 %

Versuchsvorschrift

2-{7-[4-Fluoro-2-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]imidazo[1,2-b][1,2,4]triazin-3-yl}propan-2-ol was coupled to 2-bromo-3-fluorobenzonitrile (from Example 2, step a) under the conditions described in Example 1, step e. The residue was purified by flash column chromatography (silica gel, 3% isopropyl alcohol in dichloromethane) to give the title compound in 40% yield: 1H NMR (400 MHz, CDCl3) δ 1.69 (6H, s), 3.53 (1H, s), 3.96 (3H, s), 6.96 (1H, d, J 10.3), 7.43–7.62 (3H, m), 8.11 (1H, d, J 7.9), 8.34 (1H, s), 8.71(1H, s); MS (ES+) m/z 422 [M+H]+

Aufarbeitung

  1. customThe residue was purified by flash column chromatography (silica gel, 3% isopropyl alcohol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-6029aeceb9f74bb5bb60e7e30065f86f
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07005431B2

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