HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → 1-benzyl-N-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1H-pyrazol-5-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | 1-Benzyl-1H-pyrazol-5-amine | HCID 77061 | — |
| Reactant | 4-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride) | HCID 11107815 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 1-benzyl-N-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1H-pyrazol-5-amine | HCID 67008873 | 45% |
Reaction Steps
A suspension of 1-benzyl-1H-pyrazol-5-amine (5.0 g), (4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)boronic acid (15 g), copper acetate (11 g), pyridine (12 mL) and molecular sieves 4A (10 g) in tetrahydrofuran (150 mL) was stirred for 12 hr. The reaction mixture was diluted with ethyl acetate, the insoluble material was filtered off through celite, and the filtrate was concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (4.9 g, 45%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08592431B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-f1fedc67e1ff4ffc8a2921efb16b8f0e |
| Source note | uspto-grants-2013_11 |