HuagongsheHuagongshe Chemistry Print Report · For research reference only
Nitrogen → HCID 89501152, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 2773987 | — |
| Reactant | N-(3-bromo-5-nitrophenyl)acetamide | HCID 10658908 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 89501152 | HCID 89501152 | 81% |
Reaction Steps
A solution of N-(3-bromo-5-nitrophenyl)acetamide (0.5 g, 1.9 mmol) in 1,2-dimethoxyethane (20 ml) was degassed by N2 bubbling for 5 min. 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.513 g, 2.47 mmol, 1.3 eq.) was added and the mixture was degassed for another 5 min. Pd(dppf)Cl2 (0.155 g, 0.19 mmol, 0.1 eq.) and aqueous sodium carbonate (0.5 g, 4.75 mmol, 2.5 eq.) were added and the procedure of Example 1(d) was followed. The crude residue of the product was purified by column chromatography (60-120 silica gel, 30% ethyl acetate in hexane) to give the product in 81% yield (0.4 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09447091B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-2fc925f7a43c4c1c9480a464f9be520a |
| Source note | uspto-grants-2016_09 |