HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 3,4-difluoro-N-(2-methylpyrimidin-5-yl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Trimethylboroxine | HCID 574072 | — |
| Reactant | Ica-069673 | HCID 10149311 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 3,4-difluoro-N-(2-methylpyrimidin-5-yl)benzamide | HCID 10192790 | 58.4% |
Reaction Steps
A mixture of trimethylboroxine (27 μL, 0.19 mmol), Pd(dppf)2Cl2 (22 mg, 0.019 mmol), Cs2CO3 (185 mg, 0.57 mmol) and N-(2-chloro-pyrimidin-5-yl)-3,4-difluoro-benzamide (H) (50 mg, 0.19 numol) in dioxane (1 mL)/H2O (0.1 mL) was heated at 110–130° C. (bath temperature) for 1 h. The crude reaction mixture was filtered through a pad of celite and concentrated under reduced pressure. Purification of the crude material by column chromatography (hexanes/EtOAc) gave the desired product as white solid (27 mg, 57%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07205307B2 |
| Source dataset | uspto-grants-2007_04 |
| ORD ID | ord-11e0d2f1c1f54b599ea2a3c7eceecdca |
| Source note | uspto-grants-2007_04 |