Reaktion #955924

Reaktionsgleichung

tBuOH

2-(bromomethyl)pyridine

1-ethynyl-4-methylbenzene

NaN3

→

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

Ausbeute 35.2%

Lösungsmittel

water

water

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle