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Trimethyl-2-propynylsilane → 7-Chloro-2-(4-trifluoromethoxy-benzyl)-5-trimethylsilanylethynyl-2,3-dihydro-isoindol-1-one
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Trimethyl-2-propynylsilane | HCID 83378 | — |
| 反応物 | 5-Bromo-7-chloro-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-one | HCID 11704475 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | HCID 178418476 | HCID 178418476 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 溶媒 | Diisopropylamine | HCID 7912 | — |
| 生成物 | 7-Chloro-2-(4-trifluoromethoxy-benzyl)-5-trimethylsilanylethynyl-2,3-dihydro-isoindol-1-one | HCID 57949545 | 46% |
反応手順
A mixture of 5-bromo-7-chloro-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.210 g, 0.5 mmol), PdCl2(PPh3)2 (0.019 g, 0.05 mmol), and CuI (0.010 g, 0.05 mmol) in diisopropyl amine (4 mL) was treated with trimethyl-prop-2-ynyl-silane (0.141 mL, 1 mmol) and stirred at ambient temperature for 16 h. The reaction mixture diluted with dichloromethane (20 mL) filtered and concentrated. Silica gel column chromatography using 3:1 hexane-ethyl acetate afforded 7-chloro-2-(4-trifluoromethoxy-benzyl)-5-trimethylsilanylethynyl-2,3-dihydro-isoindol-1-one (0.100 g, 46%). GC-MS: 437 (M)+, 356 (M-81)+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07968570B2 |
| 出典データセット | uspto-grants-2011_06 |
| ORD ID | ord-9446cffd7a7348488f8ab0ca792940e9 |
| 出典メモ | uspto-grants-2011_06 |