Reaction #1583836

Reaction equation

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

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   Temperatureto cool to room temperature
2. 2
   OtherThe reaction mixture was partitioned between ethyl acetate and aqueous sodium chloride
3. 3
   Otherthe layers were separated
4. 4
   Extractionthe aqueous layer was extracted with ethyl acetate (2×)
5. 5
   WashThe combined organic layers were washed with water (3×)
6. 6
   Dryingdried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated under reduced pressure

Procedure

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).

Source