HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tributylphosphine → Ethyl(6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | 1,1'-(Azodicarbonyl)dipiperidine | HCID 73042 | — |
| Reactant | (6-Hydroxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester | HCID 57431998 | — |
| Reactant | (1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanol | HCID 58456726 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Ethyl(6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetate | HCID 89768891 | 85.5% |
Reaction Steps
To a mixture of tri-n-butylphosphine (0.165 mL), (1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanol (110 mg), ethyl(6-hydroxy-1-benzothiophen-3-yl)acetate (120 mg), and THF (5.0 mL) was added ADDP (167 mg) at room temperature. The mixture was stirred at room temperature under nitrogen atmosphere overnight. 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) and then silica gel column chromatography (EtOAc/hexane) to give the title compound (173 mg). The solid was crystallized from EtOH-hexane to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09238639B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-02844995eeb64b6e8f2291c10fb419da |
| Source note | uspto-grants-2016_01 |