関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Benzenamine, 2-bromo-4-nitro- | HCID 25840 | — |
| 反応物 | Cyclopropylacetylene | HCID 138823 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | HCID 178418476 | HCID 178418476 | — |
| 溶媒 | Triethylamine | HCID 8471 | — |
| 生成物 | 2-(Cyclopropylethynyl)-4-nitroaniline | HCID 59129262 | 23,243.199% |
反応手順
To a deoxygenated solution of 2-bromo-4-nitroaniline (2.17 g, 0.01 mmol), ethynylcyclopropane (1 g, 15 mmol) and CuI (10 mg, 0.05 mmol) in triethylamine (20 mL) was added Pd(PPh3)2Cl2 (210 mg, 0.3 mmol) under N2. The mixture was heated at 70° C. and stirred for 24 hours. The solid was filtered off and washed with EtOAc (50 mL×3). The filtrate was evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=10/1) to give 2-(cyclopropylethynyl)-4-nitroaniline (470 mg, 23%). 1H NMR (300 MHz, CDCl3) δ 8.14 (d, J=2.7 Hz, 1H), 7.97 (dd, J=2.7, 9.0 Hz, 1H), 6.63 (d, J=9.0 Hz, 1H), 4.81 (brs, 2H), 1.55-1.46 (m, 1H), 0.98-0.90 (m, 2H), 0.89-0.84 (m, 2H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08952050B2 |
|---|
| 出典データセット | uspto-grants-2015_02 |
|---|
| ORD ID | ord-f447044cdfad4da5938f209789e3f71d |
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| 出典メモ | uspto-grants-2015_02 |
|---|
