Réaction #955924

Équation de réaction

tBuOH

2-(bromomethyl)pyridine

1-ethynyl-4-methylbenzene

NaN3

→

2-((4-p-Tolyl-1H-1,2,3-triazol-1-yl)methyl)pyridine

Rendement 35.2%

Solvants

water

water

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added to a microwaveable vial
2. 2
   AutreThe vial was sealed
3. 3
   Autrethe mixture was irradiated (Microwave, Personal Chemistry, Biotage from Upsala Sweden) at 125° C. for 5 min
4. 4
   Extractionthe product was extracted to EtOAc
5. 5
   Lavagewashed with 1M ammonium citrate, 0.25 M aq. HCl and brine
6. 6
   Séchagedried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Autreevaporated
9. 9
   AutreThe crude product was purified on silica gel (Eluent: 10% MeOH in DCM)

Mode opératoire

A mixture of tBuOH (1.5 mL), water (1.5 mL), 2-(bromomethyl)pyridine (253 mg, 1 mmol), 1-ethynyl-4-methylbenzene (122 mg, 1.05 mmol) and NaN3 (68 mg, 1.05 mmol) was added to a microwaveable vial. A cooper wire (50 mg) and CuSO4 (200 μl of 1M aq. solution) was added to the stirred suspension. The vial was sealed and the mixture was irradiated (Microwave, Personal Chemistry, Biotage from Upsala Sweden) at 125° C. for 5 min. The mixture was then diluted with water and the product was extracted to EtOAc, washed with 1M ammonium citrate, 0.25 M aq. HCl and brine, dried over MgSO4, filtered and evaporated. The crude product was purified on silica gel (Eluent: 10% MeOH in DCM) to give 2-((4-p-Tolyl-1H-1,2,3-triazol-1-yl)methyl)pyridine (88 mg, 35%). 1H NMR (300 MHz, dMSO): δ 2.30 (s, 3H), 5.72 (s, 2H), 7.30-7.45 (m, 4H), 7.77-7.89 (m, 3H), 8.60 (s, 1H); MS (M+H, 251).

Source