Reaktion #86356

Reaktionsgleichung

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

(6-methoxy-2-methylpyridin-3-yl)boronic acid

NaHCO3

→

TFA

title compound

Ausbeute 47.0%

4-(6-methoxy-2-methylpyridin-3-yl)-6-(trifluoromethyl)-1H-indazole

Ausbeute 47.0%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was subsequently concentrated
2. 2
   Sonstigethe crude residue was purified by preparative HPLC
3. 3
   Wascheneluting with 45% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 6.5 minutes
4. 4
   SonstigeThe volatiles were removed in vacuo

Vorschrift

A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.15 g, 0.566 mmol), (6-methoxy-2-methylpyridin-3-yl)boronic acid (0.123 g, 0.736 mmol) and PdCl2(dppf) (0.021 g, 0.028 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 microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was purified by preparative HPLC, eluting with 45% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 6.5 minutes. The volatiles were removed in vacuo to give a TFA salt of the title compound as a light brown oil (82 mg, 47%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.30 (s, 3H), 3.93 (s, 3H), 6.75-6.86 (m, 1H), 7.29 (d, J=1.26 Hz, 1H), 7.72 (d, J=8.34 Hz, 1H), 7.90-8.03 (m, 2H); ESI-MS m/z [M+H]+ calc'd for C15H12F3N3O, 308.1. found 308.15.

Quelle