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), ethynyl-cyclopropane (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 | US08598181B2 |
|---|
| 出典データセット | uspto-grants-2013_12 |
|---|
| ORD ID | ord-c60e827ce470400fbb4db0bcef8008bc |
|---|
| 出典メモ | uspto-grants-2013_12 |
|---|
