Reacción #955934

Ecuación de reacción

5-(4-ethyl-2-methoxyphenyl)-2H-1,2,4-triazole-3(4H)-thione

2-(bromomethyl)pyridine hydrobromide

→

2-((5-(4-ethyl-2-methoxyphenyl)-1H-1,2,4-triazol-3-ylthio)methyl)pyridine

Rendimiento 68.0%

Disolventes

EtOAc

EtOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed successively with water and brine
2. 2
   Secadodried over MgSO4
3. 3
   Filtraciónfiltered
4. 4
   Otroevaporated
5. 5
   OtroThe residue was purified on silica gel (Eluent: 5% MeOH in DCM)

Procedimiento

To a solution of 5-(4-ethyl-2-methoxyphenyl)-2H-1,2,4-triazole-3(4H)-thione (example 18a) (100 mg, 0.43 mmol) in EtOH (2 mL) was added 2-(bromomethyl)pyridine hydrobromide (129 mg, 0.51 mmol). The suspension was heated at 60° C. for 22 h. The reaction mixture was diluted with EtOAc and washed successively with water and brine, dried over MgSO4, filtered and evaporated. The residue was purified on silica gel (Eluent: 5% MeOH in DCM) to give 2-((5-(4-ethyl-2-methoxyphenyl)-1H-1,2,4-triazol-3-ylthio)methyl)pyridine (95 mg) as a white powder (68%). 1H NMR (300 MHz, dMSO): δ 1.19-1.22 (t, 3H), 2.63-2.69 (dd, 2H), 3.93 (s, 3H), 4.48 (s, 2H), 6.93-7.03 (m, 2H), 7.25-7.29 (m, 1H), 7.49-7.5 (m, 1H), 7.71-7.75 (m, 1H), 7.93-7.95 (d, 1H), 8.50-8,51 (d, 1H), 13.65 (bs, 1H), MS (M+H, 327).

Fuente