関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Diisopropylamine | HCID 7912 | — |
| 反応物 | 4-Bromo-2-iodoaniline | HCID 823934 | — |
| 反応物 | (R)-1-(But-3-yn-1-yl)-2-methylpyrrolidine | HCID 11367023 | — |
| 反応物 | 1-Butyn-3-yl-2-methyl-pyrrolidine | HCID 21980062 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | 5-Bromo-2-benzothiazoleethanol | HCID 21980060 | — |
| 生成物 | 4-Bromo-2-[4-(2-(R)-methyl-pyrrolidin-1-yl)-but-1-ynyl]-phenylamine | HCID 21041494 | 97.3% |
反応手順
To a solution of 1-butyn-3-yl-2-methyl-pyrrolidine in CH3CN (prepared in Example 65A assuming 100% conversion, 89 mmol) was added 4-bromo-2-iodo-phenylamine (12.0 g, 40 mmol) under nitrogen followed by addition of CuI (0.38 g, 2.0 mmol), PdCl2(PPh3) 2 (0.70 mg, 1.0 mmol) and diisopropylamine (33.6 mL, 240 mmol). The resulting solution was stirred at room temperature for 2 hours, at which time analytical HPLC analysis indicated that all 4-bromo-2-iodo-phenylamine was consumed. The solvent CH3CN was removed under vacuo and the residue was extracted with IPAC (500 mL) and 5% NaHCO3 (2×300 mL). The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give the title compound as a thick oil (11.96 g), which was used in the next step without further purification.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07094790B2 |
|---|
| 出典データセット | uspto-grants-2006_08 |
|---|
| ORD ID | ord-3e0d8478526940bf83b3ecdefee834a4 |
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| 出典メモ | uspto-grants-2006_08 |
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