Reaction #955934

Reaction equation

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

Yield 68.0%

Solvents

EtOAc

EtOH

Conditions

Workup

1. 1
   Washwashed successively with water and brine
2. 2
   Dryingdried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   Otherevaporated
5. 5
   OtherThe residue was purified on silica gel (Eluent: 5% MeOH in DCM)

Procedure

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).

Source