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Dimethylformamide → Methyl 2-(6-chloro-5-fluoropyridin-3-yloxy)-4-fluorobenzoate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Dimethylformamide | HCID 6228 | — |
| 反応物 | Methyl 2,4-Difluorobenzoate | HCID 2782897 | — |
| 反応物 | Potassium tert-butoxide | HCID 23665647 | — |
| 反応物 | 2-Chloro-3-fluoro-5-hydroxypyridine | HCID 40424737 | — |
| 溶媒 | 2-Methyltetrahydrofuran | HCID 7301 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | Methyl 2-(6-chloro-5-fluoropyridin-3-yloxy)-4-fluorobenzoate | HCID 86642876 | — |
反応手順
To a solution of 6-chloro-5-fluoropyridin-3-ol (0.977 g) in 2-methyltetrahydrofuran (12 mL) was added potassium 2-methylpropan-2-olate (1.0M in tetrahydrofuran, 7.28 mL). After stirring for 15 minutes at room temperature, methyl 2,4-difluorobenzoate (1.710 g) was added as a solution in 2-methyltetrahydrofuran (2 mL) followed by N,N-dimethylformamide (2 mL) then the reaction was heated to 75° C. under a nitrogen atmosphere. After stirring overnight the reaction was cooled, diluted with ethyl acetate (100 mL) and washed with water (50 mL) and brine (50 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (GraceResolv 40 g) eluting with a gradient of 2% to 15% ethyl acetate/hexanes gave the title compound.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US09303025B2 |
| 出典データセット | uspto-grants-2016_04 |
| ORD ID | ord-0f828f67bf0c4038b4b3ea1074c16313 |
| 出典メモ | uspto-grants-2016_04 |