関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Allyl bromide | HCID 7841 | — |
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | Tetrazolo(1,5-a)pyrimidine | HCID 349391 | — |
| 反応物 | 2-Chloro-4-fluorobenzoyl chloride | HCID 2736546 | — |
| 反応物 | N-(1-Methylpropargyl)-2-chloro-3-(trifluoromethyl)benzamide | HCID 90409423 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | 2,4-Dichlorobenzoyl chloride | HCID 66645 | 67% |
反応手順
To the suspension of Intermediate 233 (138 mg, 0.5 mmol, 1.0 equiv), tetrazolo[1,5-a]pyrimidine (Intermediate 234) (67 mg, 0.55 mmol, 1.1 equiv.), allyl bromide (73 mg, 0.6 mmol, 1.2 equiv.) and Cs2CO3(0.49 g, 1.5 mmol, 3.0 equiv.) in THF (2 mL), CuI (48 mg, 0.25 mmol, 0.5 equiv.) was added at room temperature in one portion under N2. The reaction mixture was then stirred at room temperature under N2 for 16 hours. Celite and EtOAc (5 mL) were added and the suspension was stirred for 20 minutes. The insoluble solid was filtered off and washed with EtOAc. The filtrate solution was washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography with EtOAc/hexanes as eluents to afford compound Intermediate 235 (146 mg, 0.34 mmol, 67% yield) as a white solid. Byproducts Intermediate 236 (30 mg, 0.075 mmol, 15% yield) and Intermediate 237 (2% yield) were also isolated.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09066946B2 |
|---|
| 出典データセット | uspto-grants-2015_06 |
|---|
| ORD ID | ord-e1f57e29d387476b8162e80b6fcab2a0 |
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| 出典メモ | uspto-grants-2015_06 |
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