HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium fluoride → HCID 59457671, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | tert-Butyl 4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl)piperazine-1-carboxylate | HCID 53216820 | — |
| Reactant | 7-(2-Fluoro-4-nitrophenoxy)-2-iodothieno[3,2-b]pyridine | HCID 59457661 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 59457671 | HCID 59457671 | 50.3% |
Reaction Steps
Compound 452 (22.36 g, 26.6 mmol), iodide 408 (7.904 g, 19.0 mmol), CsF (8.658 g, 57 mmol), NaHCO3 (4.788 g, 57 mmol) and Pd(PPh3)4 (2.195 g, 1.9 mmol) were combined with a mixture of H2O (25 mL) and DME (100 mL) which was with nitrogen for a half-an-hour and heated to reflux overnight. It was then was cooled to RT, diluted with EtOAc (200 ml), washed with aqueous NaHCO3 (50 mL) and brine (50 mL), and concentrated. The residue was purified by flash column chromatography (eluent pure EtOAc to 5% MeOH/EtOAc) followed by trituration with EtOAc/ether, to produce compound 453 as an off-white solid (5.4 g, 50% yield). LCMS: 565 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07790729B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-defc9140296844cdb4df74a730f2b894 |
| Source note | uspto-grants-2010_09 |