HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tributylphosphine → Methyl(7-fluoro-4-methyl-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | 1,1'-(Azodicarbonyl)dipiperidine | HCID 73042 | — |
| Reactant | (2-Methyl-6-(trifluoromethyl)pyridin-3-yl)methanol | HCID 2760122 | — |
| Reactant | Methyl(7-fluoro-6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetate | HCID 121003808 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl(7-fluoro-4-methyl-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate | HCID 89775297 | 95% |
Reaction Steps
To a mixture of tri-n-butylphosphine (0.362 mL), methyl(7-fluoro-6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetate (122.8 mg), (2-methyl-6-(trifluoromethyl)pyridin-3-yl)methanol (102 mg) and THF (4.5 mL) was added ADDP (305 mg) at room temperature. The mixture was stirred overnight at room temperature under nitrogen atmosphere. The mixture was concentrated. To the residue was added IPE and the precipitate was filtered off. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (NH, EtOAc/hexane) to give the title compound (196 mg). The compound was crystallized from EtOAc-hexane.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09238639B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-b8b7bbe26cf84bfdab1c4cd6ad01e9dd |
| Source note | uspto-grants-2016_01 |