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N,N,N',N'-Tetramethylazodicarboxamide → {6-[5-(4-Trifluoromethoxy-phenyl)-pent-4-ynyloxy]-indol-1-yl}-acetic acid ethyl ester
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | N,N,N',N'-Tetramethylazodicarboxamide | HCID 4278 | — |
| 反応物 | Tributylphosphine | HCID 13831 | — |
| 反応物 | (6-Hydroxy-indol-1-yl)-acetic acid ethyl ester | HCID 68821422 | — |
| 反応物 | 4-Pentyn-1-ol, 5-[4-(trifluoromethoxy)phenyl]- | HCID 68822690 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | {6-[5-(4-Trifluoromethoxy-phenyl)-pent-4-ynyloxy]-indol-1-yl}-acetic acid ethyl ester | HCID 68826126 | 33% |
反応手順
To an ice cold solution of (6-hydroxy-indol-1-yl)-acetic acid ethyl ester (100 mg, 455 μmol), 5-(4-trifluoromethoxy-phenyl)-pent-4-yn-1-ol (111 mg, 455 μmol) and tributylphosphine (160 μl, 546 μmol) in tetrahydrofuran (10 ml) was added N,N,N′,N′-tetramethyl azodicarboxamide (94 mg, 546 μmol). The cooling bath was removed and stirring continued for 14 h. The mixture was filtered over celite and the solvent removed under reduced pressure to give a yellow oil which was purified by column chromatography (silica gel, heptane/AcOEt) to obtain 65 mg (150 μmol, 32%) of the title compound as colorless oil.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07405236B2 |
| 出典データセット | uspto-grants-2008_07 |
| ORD ID | ord-4bc37d558c684ffb9b7c36d389bdd448 |
| 出典メモ | uspto-grants-2008_07 |