HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Bicarbonate → 4-(5-Fluoro-2-hydroxyphenyl)-1-(2-methoxyquinolin-5-ylamino)-4-methyl-2-(trifluoromethyl)pentan-2-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4-(5-Fluoro-2-methoxyphenyl)-1-(2-methoxyquinolin-5-ylamino)-4-methyl-2-(trifluoromethyl)pentan-2-ol | HCID 21948841 | — |
| Reactant | Boron tribromide dichloromethane | HCID 22277759 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-(5-Fluoro-2-hydroxyphenyl)-1-(2-methoxyquinolin-5-ylamino)-4-methyl-2-(trifluoromethyl)pentan-2-ol | HCID 21948923 | 76.8% |
Reaction Steps
100 mg (0.21 mmol) of 4-(5-fluoro-2-methoxyphenyl)-1-(2-methoxyquinolin-5-ylamino)-4-methyl-2-(trifluoromethyl)pentan-2-ol in 9 ml of CH2Cl2 is mixed at room temperature with 4 ml of 1M boron tribromide-CH2Cl2 solution. After 15 hours at room temperature, the batch is poured into saturated NaHCO3 solution, stirred for 10 minutes and extracted with ethyl acetate. The combined organic extracts are dried (Na2SO4) and concentrated by evaporation in a vacuum. Chromatography on silica gel with hexane/ethyl acetate yields 73 mg of the product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07329753B2 |
| Source dataset | uspto-grants-2008_02 |
| ORD ID | ord-ec3bf390c4fa4a4ba1a5655d16ee2950 |
| Source note | uspto-grants-2008_02 |