HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → HCID 58154518, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | HCID 58154773 | HCID 58154773 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | HCID 58154518 | HCID 58154518 | 41% |
Reaction Steps
A mixture of 2-chloro-N-(pyridin-3-yl)-3-(trifluoromethyl)quinoline-8-carboxamide (136 mg, 0.39 mmol), phenylboronic acid (62 mg, 0.51 mmol), Pd(dppf)Cl2.CH2Cl2 (39 mg, 0.048 mmol), K2CO3 (167 mg, 1.2 mmol) in dioxane/H2O (4:1, 3 ml) was heated (85° C.×2 hours) under a blanket of Nitrogen. The reaction mixture was evaporated, and the residue was triturated with ethyl acetate. The mixture was filtered, concentrated and the residue was purified by prep. HPLC to give 2-phenyl-N-(pyridin-3-yl)-3-(trifluoromethyl)quinoline-8-carboxamide as a white powder (62 mg, 41% yield). MS (ESI) calcd for C22H14F3N3O (m/z): 393.11. found: 394 [M+1].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08685970B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-c5ba08b3a4b346569d962038f2c6c055 |
| Source note | uspto-grants-2014_04 |