HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 49758339, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 6-Amino-3-chloropyridazine | HCID 21643 | — |
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 4-(Trifluoromethyl)phenylboronic acid | HCID 2734389 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1-Propanol | HCID 1031 | — |
| Product | HCID 49758339 | HCID 49758339 | 27.1% |
Reaction Steps
To a solution of 6-chloropyridazin-3-amine (3.00 g, 23.2 mmol), 4-(trifluoromethyl)phenylboronic acid (5.72 g, 30.1 mmol), cesium fluoride (9.15 g, 60.2 mmol), triethylamine (4.84 mL, 34.7 mmol) in n-propanol (100 mL) degassed with argon was added dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.953 g, 1.16 mmol), and the reaction was heated to reflux for 3 hours. Water was added to precipitate solids, which were collected by filtrations. The solids were purified on a SP1 system (0-10% MeOH in EtOAc) to yield 6-(4-(trifluoromethyl)phenyl)pyridazin-3-amine (1.5 g, 6.27 mmol, 27.1% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08785445B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-19e961eb0094495da7211963d8c806a4 |
| Source note | uspto-grants-2014_07 |