HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonia → 4-[(4-chlorobenzyl)oxy]-1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | N,N'-Dimethylethylenediamine | HCID 8070 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-one | HCID 57497864 | — |
| Reactant | 5-bromo-2-cyclopropyl-3-methyl-2H-indazole | HCID 117798640 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 4-[(4-chlorobenzyl)oxy]-1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-one | HCID 117798744 | 38.9% |
Reaction Steps
To a suspension of 5-bromo-2-cyclopropyl-3-methyl-2H-indazole (320 mg), 4-[(4-chlorobenzyl)oxy]pyridin-2(1H)-one (200 mg) and potassium carbonate (352 mg) in DMSO (20 ml) were added copper(I) iodide (162 mg) and N,N′-dimethylethylenediamine (112 mg), and the mixture was reacted at 150° C. for 1 hr under microwave irradiation. The reaction mixture was added to 28% aqueous ammonia, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol) and recrystallized from ethyl acetate to give the title compound (134 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09199963B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-b0d40714caf64cb086c2869e82d9931f |
| Source note | uspto-grants-2015_12 |