Reacción #1583836

Ecuación de reacción

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

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato cool to room temperature
2. 2
   OtroThe reaction mixture was partitioned between ethyl acetate and aqueous sodium chloride
3. 3
   Otrothe layers were separated
4. 4
   Extracciónthe aqueous layer was extracted with ethyl acetate (2×)
5. 5
   LavadoThe combined organic layers were washed with water (3×)
6. 6
   Secadodried over magnesium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated under reduced pressure

Procedimiento

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).

Fuente