Реакция #1583836

Уравнение реакции

methyl N-[(2-chloro-5-ethynylphenyl)methyl]carbamate

product

methyl N-[(2-chloro-5-ethynylphenyl)methyl]carbamate

methanol

trimethylsilyl azide

→

title compound

methyl N-[[2-chloro-5-(1H-1,2,3-triazol-5-yl)phenyl]methyl]-carbamate

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   Температураto cool to room temperature
2. 2
   ДругоеThe reaction mixture was partitioned between ethyl acetate and aqueous sodium chloride
3. 3
   Другоеthe layers were separated
4. 4
   Экстракцияthe aqueous layer was extracted with ethyl acetate (2×)
5. 5
   ПромывкаThe combined organic layers were washed with water (3×)
6. 6
   Сушкаdried over magnesium sulfate
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated under reduced pressure

Методика

To a solution of methyl N-[(2-chloro-5-ethynylphenyl)methyl]carbamate (i.e. the product of Step D) (0.43 g, 1.92 mmol) in N,N-dimethylformamide (3.9 mL) and methanol (0.4 mL) was added trimethylsilyl azide (0.38 mL, 2.89 mmol) and copper(I) iodide (0.019 g, 0.1 mmol). The reaction mixture was heated in a CEM Discover microwave apparatus at 100° C. for 8 h and then allowed to cool to room temperature. The reaction mixture was partitioned between ethyl acetate and aqueous sodium chloride, the layers were separated and the aqueous layer was extracted with ethyl acetate (2×). The combined organic layers were washed with water (3×), dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide the title compound, a compound of the present invention, as a brown solid (0.30 g).

Источник