HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tributylphosphine → Methyl(4,7-dichloro-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 | (1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanol | HCID 58456726 | — |
| Reactant | Methyl(4,7-dichloro-6-hydroxy-1-benzothiophen-3-yl)acetate | HCID 121006406 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl(4,7-dichloro-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetate | HCID 89768823 | 88.2% |
Reaction Steps
To a mixture of tri-n-butylphosphine (0.193 mL), methyl(4,7-dichloro-6-hydroxy-1-benzothiophen-3-yl)acetate (150 mg), (1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanol (102 mg) and THF (5.0 mL) was added ADDP (195 mg) at room temperature. The mixture was stirred at room temperature under nitrogen atmosphere overnight. The mixture was concentrated in vacuo. 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 (205.9 mg). The solid was crystallized from EtOAc-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-072036c0b9d54d3aa7658c3544c426c6 |
| Source note | uspto-grants-2016_01 |