HuagongsheHuagongshe Chemistry Print Report · For research reference only
p-Toluenesulfonic acid → rac-7-(2-chlorophenyl)-6-(4-chlorophenyl)-2-(3-fluorophenyl)-2H-pyrano[2,3-b]pyridin-4(3H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | 6-(2-Chlorophenyl)-5-(4-chlorophenyl)-3-[3-(3-fluorophenyl)-3-hydroxypropanoyl]pyridin-2(3H)-one | HCID 67019934 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | rac-7-(2-chlorophenyl)-6-(4-chlorophenyl)-2-(3-fluorophenyl)-2H-pyrano[2,3-b]pyridin-4(3H)-one | HCID 46890915 | — |
Reaction Conditions
| Temperature | 120 °C |
|---|
Reaction Steps
The product of step A (200 mg, 0.42 mmol) was dissolved in toluene (2 mL) and p-toluenesulfonic acid (30 mg, 0.16 mmol) was added. The reaction was heated at 120° C. for 4 h and allowed to cool overnight. The reaction was diluted with EtOAc and washed with a saturated solution of NaHCO3, brine, dried (Na2SO4), filtered and concentrated The residue was purified by flash chromatography on silica gel gradient eluted with 0-30% EtOAc in hexane to afford the title compound. (LC-2) HPLC/MS: 464.2 (M+1), 466.2 (M+3); Rt=2.61 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07999107B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-5d8e5119a5504984876cbb0a8b2da5d3 |
| Source note | uspto-grants-2011_08 |