Reacción #2496780

Ecuación de reacción

3-(trifluoromethyl)-5-(5-iodoimidazo[2,1-b][1,3,4]thiadiazol-2-yl)pyridin-2-amine

3-methoxy-4-methoxycarbonylphenylboronic acid

DCM

Na2CO3

→

desired product

Rendimiento 0.9%

4-[2-(6-Amino-5-trifluoromethyl-pyridin-3-yl)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-2-methoxy-benzoic acid methyl ester

Rendimiento 0.9%

Disolventes

DME

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe solid was filtered off
2. 2
   Lavadowashed with MeOH
3. 3
   workup.ADDITIONtreated with a mixture of DCM and MeOH
4. 4
   OtroThe solid was removed by filtration
5. 5
   Otrothe filtrate was evaporated to dryness

Procedimiento

To a suspension of 3-(trifluoromethyl)-5-(5-iodoimidazo[2,1-b][1,3,4]thiadiazol-2-yl)pyridin-2-amine (0.500 g, 1.216 mmol, 1 eq), 3-methoxy-4-methoxycarbonylphenylboronic acid (0.306 g, 1.459 mmol, 1.2 eq), Pd(dppf)Cl2.DCM (0.105 g, 0.126 mmol, 0.1 eq) in DME was added a sat. aq. solution of Na2CO3 (2 mL). The reaction mixture was heated in a sealed tube at 90° C. over the weekend. The solid was filtered off, washed with MeOH and treated with a mixture of DCM and MeOH. The solid was removed by filtration, and the filtrate was evaporated to dryness to give the desired product (0.005 g). HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=5.50 min, [M+H]+ m/z 450.1; 1H NMR (300 MHz, DMSO) δ=8.82 (d, J=1.8, 1H), 8.24 (s, 1H), 8.01 (s, 1H), 7.87 (s, 1H), 7.80 (d, J=8.1, 1H), 7.71 (d, J=8.2, 1H), 7.42 (br s, 2H), 3.95 (s, 3H), 3.80 (s, 3H) ppm.

Fuente