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 | 1-Ethynyl-1-methylcyclopropane | HCID 21590560 | — |
| 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-((1-Methylcyclopropyl)ethynyl)-4-nitroaniline | HCID 59129519 | 79% |
反応手順
To a deoxygenated solution of 2-bromo-4-nitroaniline (430 mg, 2.0 mmol) and 1-ethynyl-1-methyl-cyclopropane (630 mg, 8.0 mmol) in triethylamine (20 mL) was added CuI (76 mg, 0.40 mmol) and Pd(PPh3)2Cl2 (140 mg, 0.20 mmol) under N2. The mixture was heated at 70° C. and stirred for 24 h. 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-((1-methylcyclopropyl)ethynyl)-4-nitroaniline (340 mg, 79%). NMR (300 MHz, CDCl3) δ 8.15-8.14 (m, 1H), 7.98-7.95 (m, 1H), 6.63 (d, J=6.9 Hz, 1H), 4.80 (brs, 2H), 1.38 (s, 3H), 1.04-1.01 (m, 2H), 0.76-0.73 (m, 2H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US08623905B2 |
|---|
| 出典データセット | uspto-grants-2014_01 |
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| ORD ID | ord-9df49c113925456391c56a16c62783ca |
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| 出典メモ | uspto-grants-2014_01 |
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