関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Dimethylformamide | HCID 6228 | — |
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | Dimethylacetylene | HCID 10419 | — |
| 反応物 | 2-Iodopyridine | HCID 221126 | — |
| 反応物 | Lithium Chloride | HCID 433294 | — |
| 触媒 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 溶媒 | Methanol | HCID 887 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 溶媒 | Ammonium Chloride | HCID 25517 | — |
| 生成物 | 2,3-Dimethyl-1H-pyrrolo[2,3-c]pyridine | HCID 60026828 | 77% |
反応手順
In a pressure tube, a solution of iodopyridine (1.80 g, 8.18 mmol) in 20 mL of DMF was treated with 2-butyne (1.5 mL, 19.1 mmol), Pd(dppf)2Cl2.CH2Cl2 (357 mg, 0.438 mmol), lithium chloride (367 mg, 8.71 mmol), and sodium carbonate (1.82 g, 17.2 mmol). The tube was sealed and heated to 90° C. After 24 hours, the tube was cooled and opened. The resulting mixture was diluted with 20 mL of ethyl acetate and 20 mL of saturated aqueous ammonium chloride solution. The phases were separated and the aqueous layer was extracted with three 50 mL portions of ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (CH2Cl2 to 10% MeOH in CH2Cl2, gradient) afforded the title product as a brown solid (920 mg, 77% yield).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08741897B2 |
|---|
| 出典データセット | uspto-grants-2014_06 |
|---|
| ORD ID | ord-1b885b6059d946be93d874fc01006f08 |
|---|
| 出典メモ | uspto-grants-2014_06 |
|---|
