2-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol → 7-(4-Fluoro-2-methoxyphenyl)-α,α-dimethylimidazo[1,2-b][1,2,4]triazine-3-methanol

HRID 891865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891865
[F:1][C:2]1[CH:7]=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[C:4]([O:17][CH3:18])[CH:3]=1.Br[C:20]1[N:24]2[N:25]=[CH:26][C:27]([C:29]([OH:32])([CH3:31])[CH3:30])=[N:28][C:23]2=[N:22][CH:21]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:20]2[N:24]3[N:25]=[CH:26][C:27]([C:29]([OH:32])([CH3:30])[CH3:31])=[N:28][C:23]3=[N:22][CH:21]=2)=[C:4]([O:17][CH3:18])[CH:3]=1

Komponenten

3

Edukt 2

HCID 112076032-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-olHCID 222400914-Fluoro-2-Methoxybenzeneboronic acid pinacol ester, 96%

Produkt 1

HCID 222400807-(4-Fluoro-2-methoxyphenyl)-α,α-dimethylimidazo[1,2-b][1,2,4]triazine-3-methanolAusbeute 91 %

Versuchsvorschrift

2-(4-Fluoro-2-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane was coupled to 2-(7-bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol (from Example 1, step d) under the conditions described in Example 1, step e. The residue was purified by flash column chromatography (silica gel, EtOAc) to give the title compound in 91% yield: 1H NMR (400 MHz, CDCl3) δ 1.70 (6H, s), 3.57 (1H, s), 3.87 (3H, s), 6.78–6.83 (2H, m), 7.87 (1H, dd, J 1.6, 6.6), 8.23 (1H, s), 8.69 (1H, s); MS (ES+) m/z 303 [M+H]+.

Aufarbeitung

  1. customThe residue was purified by flash column chromatography (silica gel, EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-bbce9120f0624f10aa4d33cadf2adecf
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07005431B2

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