HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 4-Methyl-5-nitro-2,3'-bipyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Bromo-4-methyl-5-nitropyridine | HCID 345873 | — |
| Reactant | 3-Pyridinylboronic acid | HCID 2734378 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-Methyl-5-nitro-2,3'-bipyridine | HCID 46316008 | 80% |
Reaction Steps
To a solution of 2-bromo-4-methyl-5-nitropyridine (217 g, 1 mol) in DMF (2000 mL) was added Pd(dppf)Cl2 (5 g), saturated solution of Na2CO3 (200 mL) and pyridin-3-ylboronic acid (147 g, 1.2 mol). The mixture was stirred under argon for 6 h at 100. After cooling down, the solvent was removed under reduced pressure evaporation and the residue was purified by silica-gel column chromatography (mobile phase: EA:PE=1:1) to afford 4-methyl-5-nitro-2,3′-bipyridine (172 g, 80%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09260425B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-8932df7d762e40b78c799fcf4326575a |
| Source note | uspto-grants-2016_02 |