HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tributylphosphine → Methyl(4-methyl-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(6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetate | HCID 121001301 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl(4-methyl-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetate | HCID 89775282 | 74.6% |
Reaction Steps
To a mixture of tri-n-butylphosphine (0.162 mL), (1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanol (90 mg), methyl(6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetate (118 mg) and THF (5.0 mL) was added ADDP (164 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, the precipitate was filtered off, and 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 (148.4 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09238639B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-298dcd1bc4964778aa0c5ff233838e44 |
| Source note | uspto-grants-2016_01 |