Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Propargyl alcohol | HCID 7859 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | N-(5-Bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamide | HCID 59168156 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Product | Isohexane ethyl acetate | HCID 21882781 | — |
| Product | 2,3-Dichloro-N-[5-(3-hydroxy-1-propynyl)-3-methoxy-2-pyrazinyl]benzenesulphonamide | HCID 59168100 | — |
Reaction Steps
A mixture of N-(5-bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamide (Example 55a) (0.52 g), propargyl alcohol (0.223 mL), copper(I)iodide (0.05 g) and bis(triphenylphosphine)palladium(II) chloride (0.1 g) in triethylamine (3 mL) was stirred at room temperature and under nitrogen for 16 h. The solvent was evaporated. Chromatography on silica gel eluting with ethyl acetate/iso-hexane mixtures gave the title compound containing the SEM ([2-(trimethylsilyl)ethoxy]methyl) protecting group (0.38 g). 0.074 g of this compound was dissolved in dichloromethane (2 mL) and trifluoroacetic acid (2 mL). After 1 h the solvent was evaporated. Chromatography on silica gel eluting with ethyl acetate/iso-hexane mixtures gave the title compound (0.043 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07662825B2 |
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| Source dataset | uspto-grants-2010_02 |
|---|
| ORD ID | ord-d71187e891654376be20771b673cd87e |
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| Source note | uspto-grants-2010_02 |
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