HuagongsheHuagongshe Chemistry Print Report · For research reference only
Styrene → 4-[(E)-2-Phenylvinyl]-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-indazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Styrene | HCID 7501 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | 4-Bromo-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-indazole | HCID 67340730 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 4-[(E)-2-Phenylvinyl]-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-indazole | HCID 67340870 | 64.6% |
Reaction Steps
A mixture of 4-bromo-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-indazole (75 mg), styrene (33 mg), triethylamine (0.073 mL), palladium (II) acetate (2 mg) and tris(2-methylphenyl)phosphine (6 mg) in acetonitrile (2 mL) was heated for reflux under an argon atmosphere overnight. The reaction mixture was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/1-2/1) to give the title compound (50 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07998975B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-3f006803fc574b1a91dfb700b835168e |
| Source note | uspto-grants-2011_08 |