HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 4-[(4-bromobenzyl)oxy]-1-(2,3-dimethyl-2H-indazol-5-yl)pyridin-2(1H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 4-Bromobenzyl alcohol | HCID 70119 | — |
| Reactant | 1-(2,3-dimethyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one | HCID 117798670 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-[(4-bromobenzyl)oxy]-1-(2,3-dimethyl-2H-indazol-5-yl)pyridin-2(1H)-one | HCID 117798695 | 39.3% |
Reaction Steps
To a solution of 1-(2,3-dimethyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one (150 mg) in tetrahydrofuran (3 ml) were added (4-bromophenyl)methanol (110 mg), bis(2-methoxyethyl)azodicarboxylate (179 mg) and triphenylphosphine (200 mg) at room temperature, and the mixture was stirred at the same temperature for 17 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) and recrystallized from ethyl acetate to give the title compound (98 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09199963B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-b0a5d11d29444b40bda405091cb2df84 |
| Source note | uspto-grants-2015_12 |