HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 4-[3-{6-[3-Benzo[1,3]dioxol-5-yl-5-(2-difluoromethoxy-benzylcarbamoyl)-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | (2H-1,3-benzodioxol-5-yl)boronic acid | HCID 2734371 | — |
| Reactant | HCID 67338951 | HCID 67338951 | — |
| Reactant | HCID 67339165 | HCID 67339165 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 4-[3-{6-[3-Benzo[1,3]dioxol-5-yl-5-(2-difluoromethoxy-benzylcarbamoyl)-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester | HCID 67338490 | 88% |
Reaction Steps
The title compound was prepared by the same method as 4-{3-[6-(5-dimethylcarbamoyl-3′,4′-difluoro-biphenyl-3-yloxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester starting from 4-[3-{6-[3-bromo-5-(2-difluoromethoxy-benzylcarbamoyl)-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (200 mg, 0.262 mmol), 3,4-methylenedioxyphenylboronic acid (87 mg, 0.524 mmol), PdCl2(dppf) (29 mg, 0.04 mmol) and cesium carbonate (171 mg, 0.524 mmol) in 1,2-dimethoxyethane (5.0 mL) to obtain 4-[3-{6-[3-benzo[1,3]dioxol-5-yl-5-(2-difluoromethoxy-benzylcarbamoyl)-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (184 mg, 88%) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07989454B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-e4844f99931a4483ac9e3437988c2330 |
| Source note | uspto-grants-2011_08 |