Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Reactant | HCID 87426645 | HCID 87426645 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67508524 | HCID 67508524 | 28.1% |
Reaction Steps
To a stirred solution of methyl 2-chloro-5-fluoro-6-(2,2,2-trifluoroethoxy)nicotinate (1.1 g, 3.9 mmol, Step-1 of Amine-42) in THF (35 mL) is added sodium methanolate (0.32 g, 5.8 mmol) at 0° C. The mixture is stirred at 60° C. for 2 hours and cooled to room temperature. The mixture is poured into water and extracted with dichloromethane (10 mL×3). The combined organic layer is washed with water, brine, and dried over sodium sulfate. The organic solvent is removed under reduced pressure. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (9:1) to give 310 mg (28% yield) of the title compound as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09302991B2 |
|---|
| Source dataset | uspto-grants-2016_04 |
|---|
| ORD ID | ord-a8623c2907d5452c8ac011c53d831ca9 |
|---|
| Source note | uspto-grants-2016_04 |
|---|