Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | Ethyl 2-butynoate | HCID 78043 | — |
| Reactant | HCID 86661830 | HCID 86661830 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58081048 | HCID 58081048 | 61.5% |
Reaction Steps
To a solution of 5-({6-[(methylsulfonyl)methyl]pyridin-3-yl}oxy)-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carbothioamide (2.25 g) in tetrahydrofuran (10 mL) and toluene (15 mL) were added ethyl 2-butynoate (1.37 g) and tri-n-butylphosphine (0.99 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 silica gel column chromatography (methanol:ethyl acetate:hexane=0:0:100 to 5:95:0, volume ratio) to give the title compound (1.72 g, yield 61%) as a yellow amorphous solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08557805B2 |
|---|
| Source dataset | uspto-grants-2013_10 |
|---|
| ORD ID | ord-4870a286d5664c4da41c135c451e4401 |
|---|
| Source note | uspto-grants-2013_10 |
|---|