HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Ethyl 2-[2,4-difluoro-3-[[6-fluoro-3-(3-fluorophenyl)-2-methyl-phenyl]methylamino]phenoxy]acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl bromoacetate | HCID 7748 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2,4-Difluoro-3-[[6-fluoro-3-(3-fluorophenyl)-2-methyl-phenyl]methylamino]phenol | HCID 89443856 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Ethyl 2-[2,4-difluoro-3-[[6-fluoro-3-(3-fluorophenyl)-2-methyl-phenyl]methylamino]phenoxy]acetate | HCID 89444025 | 85.1% |
Reaction Steps
To a solution of 2,4-difluoro-3-[[6-fluoro-3-(3-fluorophenyl)-2-methyl-phenyl]methylamino]phenol (230 mg, 0.63 mmol, 1.0 eq) in DMF (4 mL) was added Cs2CO3 (420 mg, 1.2 mmol, 2 eq). The reaction was stirred for 10 min, then ethyl bromoacetate (130 mg, 0.76 mmol, 1.2 eq) was added. The reaction mixture was stirred for a further 30 min, then water was added and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with water, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography (petroleum ether: EtOAc, 25:1) to give title compound as a colourless oil (240 mg, 85%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09249085B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-2c0f48d6e82b4a76a369304aea48abcf |
| Source note | uspto-grants-2016_02 |