Réaction #2000274

Équation de réaction

8-(3-(trifluoromethyl)phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-amine

methyl 4-iodobenzoate

cesium carbonate

→

methyl 4-(8-(3-(trifluoromethyl)phenyl)[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoate

Rendement 72.1%

Solvants

1,4-dioxane

Conditions de réaction

Traitement

1. 1
   Concentrationthe reaction mixture was concentrated in vacuo
2. 2
   workup.ADDITIONthe resulting residue was diluted with methanol and water
3. 3
   FiltrationThe solid was collected by filtration
4. 4
   Lavagerinsed sequentially with water, isopropanol, and hexanes

Mode opératoire

A suspension of 8-(3-(trifluoromethyl)phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-amine (1.0 g, 3.6 mmol, 1 equiv), methyl 4-iodobenzoate (0.95 g, 3.6 mmol, 1.0 equiv), palladium (II) acetate (0.080 g, 0.36 mmol, 0.10 equiv), cesium carbonate (2.34 g, 7.18 mmol, 2.0 equiv), and Xantphos (0.10 g, 0.17 mmol, 0.047 equiv) in 1,4-dioxane (20 mL) was heated to 80° C. After 16 h, the reaction mixture was concentrated in vacuo, and the resulting residue was diluted with methanol and water. The solid was collected by filtration and rinsed sequentially with water, isopropanol, and hexanes to afford crude methyl 4-(8-(3-(trifluoromethyl)phenyl)[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoate (1.07 g, 72%). LCMS (ESI) m/z: 413.0; 1H NMR (400 MHz, DMSO-d6) δ: 10.29 (s, 1 H), 8.88 (m, 1 H), 8.63 (s, 1 H), 8.40 (m, 1 H), 8.02 (m, 1 H), 7.78-7.90 (m, 6 H), 7.20 (m, 1 H), 3.80 (s, 3 H).

Source