HuagongsheHuagongshe Chemistry Print Report · For research reference only
8-Hydroxyquinoline → HCID 66969204, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 8-Hydroxyquinoline | HCID 1923 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-(Bromoacetyl)benzonitrile | HCID 98654 | — |
| Reactant | 4-Bromo-1-chloro-2-iodobenzene | HCID 51000071 | — |
| Reactant | HCID 178509600 | HCID 178509600 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | N,N-Dimethylformamide--water (1/1) | HCID 21962138 | — |
| Product | HCID 66969204 | HCID 66969204 | — |
Reaction Steps
The compound was prepared according to Liu et al. J. Org. Chem. 2005, 70, 10135. 4-(1H-Imidazol-4-yl)-benzonitrile (75 mg, 0.44 mmol; prepared from 4-(2-bromo-acetyl)-benzonitrile using the method of Lynch et al. J. Am. Chem. Soc. 1994, 116, 11030), 4-bromo-1-chloro-2-iodobenzene (169 mg, 0.532 mmol), Cs2CO3 (577 mg, 1.77 mmol), CuI (3 mg, 0.013 mmol), 8-hydroxyquinoline (2 mg, 0.013 mmol), and DMF/H2O (2 mL; 10:1 solution) were combined in a 10 mL CEM Microwave reaction vessel fitted with magnetic stir bar and subjected to microwave irradiation at 150° C. for 30 min. The contents were then filtered and concentrated to dryness affording intermediate 5-bromo-2-chlorophenyl)-1H-imidazol-4-yl]-benzonitrile (68 mg, 43%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08674109B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-b7257fe353b94c66bc708b009f30f804 |
| Source note | uspto-grants-2014_03 |