HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → HCID 71295244, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Pyrazole, 4-amino-, hydrochloride | HCID 78034 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | HCID 86729194 | HCID 86729194 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | tert-Butanol | HCID 6386 | — |
| Product | HCID 71295244 | HCID 71295244 | 91.4% |
Reaction Steps
A solution of 5-(2-chloropyridin-4-yl)-2-cyclopropylmethoxybenzonitrile (0.25 g, 0.0878 mmol) in t-butanol (5 ml) is degassed with nitrogen for 5 min. 1H-Pyrazol-4-ylamine hydrochloride (0.12 g, 1.08 mmol), Josiphos (24.3 mg, 0.00439 mmol) and tris(dibenzylideneacetone)dipalladium(0) (40.0 mg, 0.00439 mmol) is then added. A solution of 1.6M lithium bis(trimethylsilyl)amide in THF (0.35 g, 2.1 mmol) is added dropwise. The mixture is irradiated in the microwave at 140° C. for 2 h. 30 ml of water are then added, and the mixture is filtered. The crude product is purified by chromatography, giving 26.6 mg of the desired product as brown solid;
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08969335B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-d4edc4b65c034d38a8424f74c42f41c5 |
| Source note | uspto-grants-2015_03 |