HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 4-[3-{6-[5-(3,3-Difluoro-pyrrolidine-1-carbonyl)-3'-fluoro-biphenyl-3-yloxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Fluorophenylboronic acid | HCID 2733986 | — |
| Reactant | HCID 67337985 | HCID 67337985 | — |
| 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-[5-(3,3-Difluoro-pyrrolidine-1-carbonyl)-3'-fluoro-biphenyl-3-yloxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester | HCID 67338203 | 97% |
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-(3,3-difluoro-pyrrolidine-1-carbonyl)-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (112 mg, 0.16 mmol), 3-fluorophenylboronic acid (45.23 mg, 0.32 mmol), PdCl2(dppf) (17.63 mg, 0.024 mmol) and cesium carbonate (105.6 mg, 0.32 mmol) in 1,2-dimethoxyethane (5.0 mL) to obtain 4-[3-{6-[5-(3,3-difluoro-pyrrolidine-1-carbonyl)-3′-fluoro-biphenyl-3-yloxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (111 mg, 97%) 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-00ed97b79d2543eebb8e340580266e45 |
| Source note | uspto-grants-2011_08 |