HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → HCID 68225764, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (5-Fluoropyridin-3-yl)boronic acid | HCID 44717403 | — |
| Reactant | HCID 86658169 | HCID 86658169 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 68225764 | HCID 68225764 | — |
Reaction Steps
A solution of 5-fluoropyridin-3-ylboronic acid (0.096 g, 0.68 mmol), (S)-benzyl 1-(6-fluoro-3-iodoimidazo[1,2-a]pyridin-2-yl)ethylcarbamate (0.200 g, 0.455 mmol), sodium carbonate (0.145 g, 1.366 mmol), and 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride, 1:1 complex with DCM (0.019 g, 0.023 mmol) in dioxane (2.53 mL) and water (0.50 mL) was stirred at 110° C. under microwave irradiation for 2 h. Purification by MPLC (eluted with a gradient of 10-60% EtOAc in hexanes) afforded crude (S)-benzyl 1-(6-fluoro-3-(5-fluoropyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)ethylcarbamate as an off-white foam. LC-MS (ESI) m/z 409.1 [M+H]
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08575183B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-814db9cc44b941f2920819a471871357 |
| Source note | uspto-grants-2013_11 |