Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | Ethyl 2-butynoate | HCID 78043 | — |
| Reactant | 7-Methyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carbothioamide | HCID 86661838 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 58081030 | HCID 58081030 | 76% |
Reaction Steps
To a mixed solution of 7-methyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carbothioamide (2.6 g), ethyl 2-butynoate (1.7 mL), tetrahydrofuran (40 mL), and toluene (60 mL) was added tri-n-butylphosphine (2.2 mL) under an argon atmosphere at room temperature, and the mixture was stirred at 40° C. for 2.5 hr. The reaction solution was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=40:60 to 65:35, volume ratio) to give the title compound (2.59 g, yield 76%) as a pale-yellow amorphous solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08557805B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-6fae6e65e40240ecb20d7fc3654c296c |
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| Source note | uspto-grants-2013_10 |
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