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Ethyl Acetate → 6-Bromo-3-[[2-(trimethylsilyl)ethoxy]methyl]-3H-imidazo[4,5-b]pyridine
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Ethyl Acetate | HCID 8857 | — |
| 反応物 | Sodium Hydroxide | HCID 14798 | — |
| 反応物 | 6-Bromo-4H-imidazo[4,5-b]pyridine | HCID 911578 | — |
| 反応物 | 2-Chloromethyl 2-(trimethylsilyl)ethyl ether | HCID 2724271 | — |
| 触媒 | Benzyl triethylammonium chloride | HCID 66133 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 溶媒 | Hexane | HCID 8058 | — |
| 生成物 | 6-Bromo-3-[[2-(trimethylsilyl)ethoxy]methyl]-3H-imidazo[4,5-b]pyridine | HCID 19358288 | 14.4% |
反応手順
(2-Chloromethoxy-ethyl)-trimethyl-silane (508.6 mg, 3.0456 mmol), catalytic amount of benzyl triethyl-ammonium chloride and NaOH (203.04 mg, 5.076 mmol) were added to a solution of 6-bromo-3H-imidazo[4,5-b]pyridine (500 mg, 2.538 mmol) in DCM (10 mL) at 0° C. The resulting mixture was stirred room temperature for 6 hours. The reaction was monitored by TLC (80% ethylacetate in hexane). The reaction mixture was partitioned between DCM and water. The organic layer was washed with water, brine, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (20% ethylacetate in hexane) afforded 120 mg of the product (14.4% yield).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | USRE045173E1 |
| 出典データセット | uspto-grants-2014_09 |
| ORD ID | ord-486874dd47bb489285c1af4af84829f7 |
| 出典メモ | uspto-grants-2014_09 |