Реакция #955924

Уравнение реакции

tBuOH

2-(bromomethyl)pyridine

1-ethynyl-4-methylbenzene

NaN3

→

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

Выход 35.2%

Растворители

water

water

Условия реакции

Обработка

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

Методика

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).

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