反応式
[H-].[Na+].C(OP([CH2:11][C:12](=[O:17])[N:13]([O:15][CH3:16])[CH3:14])(=O)OCC)C.[NH:18]1[C:26]2[C:21](=[CH:22][C:23]([CH:27]=O)=[CH:24][CH:25]=2)[CH:20]=[CH:19]1.N1C2C(=CC=CC=2)C=C1>C1COCC1>[CH3:16][O:15][N:13]([CH3:14])[C:12](=[O:17])[CH:11]=[CH:27][C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][CH:24]=1)[NH:18][CH:19]=[CH:20]2参加物
実験手順
A mixture of sodium hydride (0.44 g of a 60% suspension in mineral oil, 11 mmol) and diethyl-(N-methoxy-N-methyl-carbamoylmethyl)-phosphonate (3.0 g, 3 equiv.) in anhydrous THF was stirred at room temperature for 30 minutes. A solution of indole-5-carboxaldehyde (0.61 g, 4.18 mmol) was added dropwise to the mixture. The reaction was complete after 2 h after the addition of the starting indole. The mixture was quenched with water (50 ml), then diluted with ether. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give N-methoxy-N-methyl-3-(indol-5-yl)acrylamide as a yellow oil which solidified on standing to an off-white solid (1.53 g, quantitative yield. 1H NMR (CDCl3): δ8.55 (br, 1H), 7.87 (d, J=18.6 Hz, 1H), 7.85 (s, 1H), 7.38 (d, J=8.5 Hz, 1H), 7.25 (d, J=8.5 Hz, 1H), 7.23 (m, 1H), 7.0 (d, J=18.6 Hz, 1H), 6.58 (m, 1H), 3.78 (s, 3H), and 3.32 (s, 3H). FIMS: 229.1 (M−H)−, reverse-phase HPLC purity: 88%.
後処理
- waitThe reaction was complete after 2 h
- customThe mixture was quenched with water (50 ml)
- additiondiluted with ether
- customThe organic layer was separated
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
出典と根拠
- ORDレコード
- ord-5a8ba1de68ef42b4918e2efe72737d08
- 出典データセット
- uspto-grants-2004_08
- 特許番号
- US06777437B2
関連ノート
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