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2,5-Dibromopyridine → Benzyl 3-(5-bromopyridin-2-yl)prop-2-ynylcarbamate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 2,5-Dibromopyridine | HCID 69353 | — |
| 反応物 | Benzyl prop-2-yn-1-ylcarbamate | HCID 11137906 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | HCID 178418476 | HCID 178418476 | — |
| 溶媒 | Diisopropylamine | HCID 7912 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | Benzyl 3-(5-bromopyridin-2-yl)prop-2-ynylcarbamate | HCID 21299382 | 73.8% |
反応手順
A mixture of 2,5-dibromopyridine (1.19 g), N-Cbz-propargylamine (1.04 g), Pd(PPh3)2Cl2 (73 mg), and CuI (10 mg) in diisopropylamine (20 mL) was stirred at ambient temperature for 3 hours under nitrogen. The mixture was diluted with ethyl acetate (50 mL). The mixture was filtered and washed with ethyl acetate (20 mL). The filtrate and wash were combined, concentrated under reduced pressure and triturated in MTBE to give crystalline 7-1 (1.28 g). The mother liquor was further purified by silica gel column chromatography using a mixture of MTBE: hexanes (1:1) to give an additional 280 mg of 7-1.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06706885B2 |
| 出典データセット | uspto-grants-2004_03 |
| ORD ID | ord-26c2d7fafdc044be956e21bc0a6f0e9f |
| 出典メモ | uspto-grants-2004_03 |