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Cesium carbonate → 6-bromo-1'-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate | HCID 7033050 | — |
| 反応物 | 6-bromospiro[1-benzofuran-3,3'-indol]-2'(1'H)-one | HCID 46194050 | — |
| 溶媒 | Methyl Ethyl Ketone | HCID 6569 | — |
| 生成物 | 6-bromo-1'-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one | HCID 59352333 | 101.7% |
反応手順
To a stirred solution of 6-bromospiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (1.3 g, 4.3 mmol) in 2-butanone (40.0 mL) was added cesium carbonate (4.2 g, 12.9 mmol) and (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate (1.4 g, 5.4 mmol). The reaction was refluxed for 16 h, filtered and concentrated in vacuo to dryness. The residue was purified by flash chromatography with 25% ethyl acetate in hexanes to afford 6-bromo-1′-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (1.75 g, 100%) as a colorless solid: MS (ES+) m/z 400.0 (M+1), 402.0 (M+1).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08101647B2 |
| 出典データセット | uspto-grants-2012_01 |
| ORD ID | ord-9a7ffba37537471f93292c4d2011ebb5 |
| 出典メモ | uspto-grants-2012_01 |