Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | Ethyl 2-butynoate | HCID 78043 | — |
| Reactant | HCID 86652848 | HCID 86652848 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 66898283 | HCID 66898283 | 55% |
Reaction Steps
A mixture of 7-[2-methoxy-1-(methoxymethyl)ethoxy]-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indole-2-carbothioamide (1.69 g), ethyl 2-butynoate (0.84 mL), tributylphosphine (0.9 mL), tetrahydrofuran (20 mL) and toluene (30 mL) was stirred at 50° C. for 13 h. The mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (methanol/ethyl acetate/hexane=0/20/80 to 5/95/0, volume ratio), followed by basic silica gel column chromatography (ethyl acetate/hexane=20/80 to 90/10, volume ratio) to give the title compound (1.14 g, 55%) as a brownish amorphous solid. MS 578 (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-05ccbfbeed074b529a1c4e5fec81f998 |
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| Source note | uspto-grants-2014_03 |
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