HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyrazole → methyl 6-(1H-pyrazol-1-yl)picolinate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyrazole | HCID 1048 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | trans-N,N'-dimethyl-1,2-cyclohexanediamine | HCID 2733821 | — |
| Reactant | Methyl 6-bromopyridine-2-carboxylate | HCID 16217886 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | methyl 6-(1H-pyrazol-1-yl)picolinate | HCID 69083337 | — |
Reaction Steps
A mixture of commercially available methyl 6-bromopicolinate (1.000 g; 4.62 mmol), 1H-pyrazole (315 mg; 4.62 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (135 mg; 0.92 mmol), K2CO3 (1.370 g; 9.72 mmol), and CuI (44 mg; 0.23 mmol) in anh. toluene (15 ml) was heated at reflux for 17 h. After cooling to rt, water was added, and the mixture was extracted with AcOEt. The mixed organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=20/1) afforded methyl 6-(1H-pyrazol-1-yl)picolinate as a colorless solid. LC-MS (conditions A): tR=0.59 min.; [M+H]+: 204.04 g/mol.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09242970B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-2d6d409504ff4c8c81c486c7af79c570 |
| Source note | uspto-grants-2016_01 |