HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → HCID 58913281, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Thiophene-3-boronic acid | HCID 581760 | — |
| Reactant | Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate | HCID 10991161 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 58913281 | HCID 58913281 | 71.6% |
Reaction Steps
To a solution of tert-butyl 4-{[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-1(2H)-carboxylate (610 mg) in 1,2-dimethoxyethane (15 ml) was added 3-thienylboronic acid (353 mg), tetrakis(triphenylphosphine) palladium (106 mg) and aq. 2M cesium carbonate solution (2.7 ml) and the mixture was refluxed 2 hours under nitrogen atmosphere. After removal of solvent in vacuo, the residue was extracted by EtOAc. The extract was washed with brine, dried over MgSO4 and concentrated in vacuo. The resultant residue was purified by silica gel column (n-hexane:EtOAc=80:20) to give tert-butyl 4-(3-thienyl)-3,6-dihydropyridine-1(2H)-carboxylate (350 mg) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08603975B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-20d7266fbabb48f583524e5b5ba2df0e |
| Source note | uspto-grants-2013_12 |