반응 #955924

반응 방정식

tBuOH

2-(bromomethyl)pyridine

1-ethynyl-4-methylbenzene

NaN3

→

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

수율 35.2%

용매

water

water

반응 조건

후처리

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

실험 절차

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).

출처