HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → tert-butyl 4-[3-(acetylamino)phenyl]-3,6-dihydro-1(2H)-pyridinecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (3-Acetamidophenyl)boronic acid | HCID 157274 | — |
| Reactant | Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate | HCID 10991161 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | tert-butyl 4-[3-(acetylamino)phenyl]-3,6-dihydro-1(2H)-pyridinecarboxylate | HCID 21957188 | — |
Reaction Steps
The reaction of saturated of aqueous Na2CO3 solution (25 mL), tert-butyl 4-{[(trifluoromethyl)sulfonyl]oxy}-1,2,3,6-tetrahydro-1-pyridine-carboxylate (20 mmol), 3-acetamidophenylboronic acid (30 mmol) and tetrakistriphenylphosphine palladium (0) (1.15 g) in dimethoxyethane (40 mL) at reflux temperature overnight gave tert-butyl 4-[3-(acetylamino)phenyl]-3,6-dihydro-1(2H)-pyridinecarboxylate. Deprotection of the BOC group using HCl in dioxane followed by basification (pH 11–12) gave the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07067534B1 |
| Source dataset | uspto-grants-2006_06 |
| ORD ID | ord-96e413e9ba0a4f2cb8a67268b7050a3a |
| Source note | uspto-grants-2006_06 |