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 | HCID 178418476 | HCID 178418476 | — |
| 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 | US08106088B2 |
|---|
| 出典データセット | uspto-grants-2012_01 |
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| ORD ID | ord-cfbb316b18b04b36b5c4ecb90b566b21 |
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| 出典メモ | uspto-grants-2012_01 |
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