Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 2773987 | — |
| Reactant | HCID 86707406 | HCID 86707406 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | HCID 86707407 | HCID 86707407 | 84.4% |
Reaction Steps
A solution of tert-butyl (3S)-1-(1-(3-(7-bromo quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ylcarbamate (Example 2, Step A; 0.18 g, 0.30 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.127 g, 0.61 mmol), PdCl2(dppf)*dcm (0.0249 g, 0.030 mmol), and triethylamine (0.064 mL, 0.46 mmol) in IPA (3 mL) was heated at 100° C. for 3 hours. After cooling to ambient temperature, the residue was directly purified by C-18 reverse phase flash chromatography (Biotage SP4 unit, C-18 25M column, 10-90% CH3CN/water gradient; 30 CV) to give tert-butyl (3S)-1-(2,2,2-trifluoro-1-(3-(7-(1-methyl-1H-pyrazol-4-yl)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (0.15 g, 83.2%) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08889704B2 |
|---|
| Source dataset | uspto-grants-2014_11 |
|---|
| ORD ID | ord-58a4600ba4344570a89a2c81597196d8 |
|---|
| Source note | uspto-grants-2014_11 |
|---|
