Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | Ethyl 2-butynoate | HCID 78043 | — |
| Reactant | HCID 86661827 | HCID 86661827 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 58081013 | HCID 58081013 | 32.5% |
Reaction Steps
To a solution of 5-({6-[(2-methoxyethoxy)methyl]pyridin-3-yl}oxy)-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carbothioamide (1.1 g) in tetrahydrofuran (10 mL) and toluene (15 mL) were added ethyl 2-butynoate (0.67 g) and tri-n-butylphosphine (0.49 g), and the mixture was stirred at 90° C. for 1 hr. The reaction mixture was cooled, and concentrated under reduced pressure. The obtained crude product was subjected to basic silica gel column chromatography (ethyl acetate:hexane=0:100 to 50:50, volume ratio) to give the title compound (445 mg, yield 32%) as a yellow oil.
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-e575024723ad41c98f82c5aad6ec78dd |
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| Source note | uspto-grants-2013_10 |
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