HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phenylboronic Acid → N-Boc-2-phenyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | tert-Butyl 2-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate | HCID 19365864 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | N-Boc-2-phenyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine | HCID 19365863 | — |
Reaction Steps
A solution of N-Boc-2-bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (Step 1; 637 mg, 0.2 mmol), phenyl boronic acid (244 mg, 0.2 mmol), NaHCO3 (504 mg, 6 mmol) and tetrakis(triphenylphosphine)palladium(O) (116 mg, 0.1 mmol) in DME (10 mL) and water (10 mL) was heated to 80° C. for 20 h. The mixture was partitioned between water and EtOAc, washed with aqueous NaHCO3, water (2×) then brine, dried and evaporated. Column chromatography of the residue (silica gel; hexane/EtOAc 95:5) afforded the title compound as a viscous oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06015817 |
| Source dataset | uspto-grants-2000_01 |
| ORD ID | ord-befedb2b7d194db6b8c81d6b9b809980 |
| Source note | uspto-grants-2000_01 |