Reaktion #86368

Reaktionsgleichung

4-bromo-6-(trifluoromethyl)-1H-indazole

(2-methoxy-5-(methoxycarbonyl)phenyl)boronic acid

→

title compound

Ausbeute 71.0%

methyl 4-methoxy-3-(6-(trifluoromethyl)-1H-indazol-4-yl)benzoate

Ausbeute 71.0%

Lösungsmittel

dioxane

NaHCO3

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was subsequently concentrated
2. 2
   workup.ADDITIONthe crude residue was diluted with DCM
3. 3
   Waschenwashed with water
4. 4
   Einengenconcentrated
5. 5
   Sonstigepurified by CombiFlash® chromatography
6. 6
   Wascheneluting with a gradient of 0-40% MeOH in DCM over a period of 200 minutes
7. 7
   Einengenconcentrated

Vorschrift

A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.631 g, 2.381 mmol), (2-methoxy-5-(methoxycarbonyl)phenyl)boronic acid (0.5 g, 2.381 mmol) and PdCl2(dppf) (0.087 g, 0.119 mmol) in dioxane (10 mL) and aqueous saturated NaHCO3 (3 mL). The resulting light brown suspension was heated at 140° C. for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was diluted with DCM and washed with water, concentrated, and then purified by CombiFlash® chromatography, eluting with a gradient of 0-40% MeOH in DCM over a period of 200 minutes. The product-containing fractions were combined and concentrated to give the title compound as a light brown solid (0.592 g, 71.0%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.85 (s, 3H), 3.84 (s, 3H), 7.21-7.46 (m, 2H), 7.89-7.99 (m, 3H), 8.10 (dd, J=8.59, 2.27 Hz, 1H), 13.62 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C17H13F3N2O3, 351.1. found 351.16.

Quelle