Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Methanol | HCID 887 | — |
| Edukt | Azidotrimethylsilane | HCID 78378 | — |
| Edukt | methyl N-[(2-chloro-5-ethynylphenyl)methyl]carbamate | HCID 86641518 | — |
| Katalysator | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | HCID 178502068 | HCID 178502068 | — |
Reaktionsschritte
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).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08822521B2 |
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| Quelldatensatz | uspto-grants-2014_09 |
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| ORD ID | ord-35a6f0c7e97740369673e373933633cd |
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| Quellennotiz | uspto-grants-2014_09 |
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