Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | Ethyl 2-butynoate | HCID 78043 | — |
| Reactant | HCID 58236986 | HCID 58236986 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 58236985 | HCID 58236985 | 72% |
Reaction Steps
To a stirred solution of 7-methoxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carbothioamide (0.69 g), ethyl 2-butynoate (0.43 mL), tetrahydrofuran (15 mL) and toluene (25 mL) was added tributylphosphine (0.54 mL) at room temperature under argon atmosphere. After the mixture was stirred at 40° C. for 4 h, ethyl 2-butynoate (0.22 mL) and tributylphosphine (0.27 mL) were added thereto. After stirring at 40° C. for 2 h, the reaction mixture was concentrated to give a light brown oil, which was purified by silica gel chromatography (ethyl acetate:hexane=30:70 to 75:25, volume ratio) to give the title compound (684 mg, 72%) as a light yellow oil. MS 489 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08673942B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-7e91ad4f29d54b5ebfa6446cd8e7b288 |
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| Source note | uspto-grants-2014_03 |
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