تفاعل #955924

معادلة التفاعل

tBuOH

2-(bromomethyl)pyridine

1-ethynyl-4-methylbenzene

NaN3

→

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

المردود 35.2%

المذيبات

water

water

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر