HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Phosphate, Tribasic → 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 2-Bromo-5-methylpyridine | HCID 564216 | — |
| Reactant | Methyl 3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate | HCID 44119765 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water 1,2-dimethoxyethane | HCID 18180031 | — |
| Product | 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester | HCID 57851658 | 40% |
Reaction Steps
To a solution of 2-bromo-5-methylpyridine (1.24 g, 7 mmol), Pd(PPh3)4 (226 mg, 0.2 mmol) and K3PO4 (2.76 g, 13 mmol) in DME/H2O (5 ml/1 ml) was added 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.00 g, 6.5 mmol) under N2 atmosphere. The mixture was subjected to microwave radiation at 130° C. for 0.5 hours. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (CH2Cl2/MeOH) to give 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (700 mg, 40%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08895589B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-5a204e29b5c2479fba1cdcb6cdb90ef5 |
| Source note | uspto-grants-2014_11 |