Reaction #955924

Reaction equation

tBuOH

2-(bromomethyl)pyridine

1-ethynyl-4-methylbenzene

NaN3

→

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

Yield 35.2%

Solvents

water

water

Conditions

Workup

1. 1
   workup.ADDITIONwas added to a microwaveable vial
2. 2
   OtherThe vial was sealed
3. 3
   Otherthe 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
   Washwashed with 1M ammonium citrate, 0.25 M aq. HCl and brine
6. 6
   Dryingdried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Otherevaporated
9. 9
   OtherThe crude product was purified on silica gel (Eluent: 10% MeOH in DCM)

Procedure

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