HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → 6-(4-Fluorophenylamino)phthalazin-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 4-Fluoroaniline | HCID 9731 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | HCID 178518884 | HCID 178518884 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | 2-Methyltetrahydrofuran | HCID 7301 | — |
| Product | 6-(4-Fluorophenylamino)phthalazin-1-ol | HCID 178518906 | — |
Reaction Steps
A mixture of 6-bromophthalazin-1-ol (1.00 g, 4.44 mmol), 4-fluorobenzenamine (0.642 g, 5.78 mmol), Pd(dppf)Cl2.CH2Cl2 (0.130 g, 0.178 mmol), and lithium bis(trimethylsilyl)amide (2.23 g, 13.3 mmol) in 2-methyltetrahydrofuran (10 mL) was heated at 95° C. in an oil bath for 24 h in a sealed tube. The mixture was cooled to RT, diluted with MeOH and filtered through a pad of Celite. The filtrate was concentrated over silica gel. The residue was purified using column chromatography (0-4% MeOH in CH2Cl2) to yield the title compound as a yellow crystalline solid. MS (ESI, pos. ion) m/z: 256.0 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08497269B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-c80fc78b1a544d2187cd9205e15bca72 |
| Source note | uspto-grants-2013_07 |