関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | 3,3-Dimethyl-1-butyne | HCID 13512 | — |
| 反応物 | tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamate | HCID 53415320 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | HCID 178418476 | HCID 178418476 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 生成物 | [6-Chloro-4-(3,3-dimethyl-but-1-ynyl)-pyridin-3-yl]-carbamic acid tert-butyl ester | HCID 57908146 | 78% |
反応手順
To a deoxygenated solution of (6-chloro-4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester (23.3 g, 65.6 mmol), 3,3-dimethyl-but-1-yne (53.8 g, 0.656 mol), CuI (623 mg, 3.3 mmol) and triethylamine (13.3 g, 0.13 mol) in toluene (150 mL) and water (50 mL) was added Pd(PPh3)2Cl2 (2.30 g, 3.28 mmol) under N2. The mixture was heated at 70° C. and stirred for 24 hours. The solid was filtered off and washed with ethyl acetate (200 mL×3). The filtrate was evaporated under reduced pressure to obtain a residue, which was purified by column (petroleum ether/ethyl acetate=10/1) to give [6-chloro-4-(3,3-dimethyl-but-1-ynyl)-pyridin-3-yl]-carbamic acid tert-butyl ester (15.8 g, 78%). 1H NMR (300 MHz, CDCl3) δ 9.10 (br s, 1H), 7.21 (s, 1H), 6.98 (br s, 1H), 1.53 (s, 9H), 1.36 (s, 9H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09102672B2 |
|---|
| 出典データセット | uspto-grants-2015_08 |
|---|
| ORD ID | ord-625d21f062fd45b0ae63ef512db8e683 |
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| 出典メモ | uspto-grants-2015_08 |
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