HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 7-(2-fluoro-4-nitrophenoxy)-N-(3-methoxyphenyl)thieno[3,2-b]pyridin-2-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Methoxyaniline | HCID 10824 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 7-(2-Fluoro-4-nitrophenoxy)-2-iodothieno[3,2-b]pyridine | HCID 59457661 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 7-(2-fluoro-4-nitrophenoxy)-N-(3-methoxyphenyl)thieno[3,2-b]pyridin-2-amine | HCID 59457684 | 59% |
Reaction Steps
A solution of 399 (scheme 87) (700 mg, 1.68 mmol), Cs2CO3 (1.12 g, 3.43 mmol), 3-methoxyaniline (190 μL, 206 mg, 1.68 mmol), Pd(OAc)2 (70 mg, 0.17 mmol) and Xantphos (1.43 g, 2.52 mmol) (J. Org. Chem., 1999, 64, 6019-6022) in dioxane (15 mL) was heated to reflux for 5 hrs. The reaction mixture was cooled, concentrated and the residue was purified by flash chromatography using 80% EtOAc in hexanes as the eluent, to afford 403 (408 mg, 59% yield). MS (m/z): (M+1) 412.0 (100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08093264B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-fa750a219dd04d45ae39e8d44f6f5fd6 |
| Source note | uspto-grants-2012_01 |