反応式
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[N:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH:13][C:6]=12)=O.C[N:23]([CH:25]=O)C.[C:27]([O-])(=O)[C:28]([CH3:31])(C)[CH3:29].[Cs+].C([O-])(=O)C.[NH4+:39]>O>[C:28]([C:25]1[NH:23][C:3]([C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[N:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH:13][C:6]=23)=[CH:2][N:39]=1)([CH3:31])([CH3:29])[CH3:27]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
実験手順
To a solution of 2-chloro-1-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)ethanone (prepared, e.g., as in Ex. 50, Step 1) (0.054 g, 0.00017 mol) in DMF (1.8 mL, 0.023 mol) was added cesium pivalate (0.0389 g, 0.000166 mol) and the reaction was stirred at room temperature for 16 hours. Ammonium acetate (0.45 g, 0.0058 mol) was added, and the reaction was heated in the microwave to 170° C. for 5 minutes. Water was added and the product was extracted with MTBE. The combined organic extracts were dried over sodium sulfate, then filtered and concentrated. The crude residue was purified by flash column chromatography (2.5% MeOH/DCM) to yield 4-(2-tert-butyl-1H-imidazol-5-yl)-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine (32 mg, 52%). 1H NMR (400 MHz, CDCl3): 8.31 (d, 1H), 7.50 (s, 1H), 7.40 (d, 1H), 7.37 (d, 1H), 6.94 (d, 1H), 5.69 (s, 2H), 3.52 (dd, 2H), 1.46 (s, 9H), 0.90 (dd, 2H), −0.08 (s, 9H); MS(ES): 371 (M+1).
後処理
- temperaturethe reaction was heated in the microwave to 170° C. for 5 minutes
- extractionthe product was extracted with MTBE
- dry with materialThe combined organic extracts were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude residue was purified by flash column chromatography (2.5% MeOH/DCM)
出典と根拠
- ORDレコード
- ord-89b3030e1aee43b69129a8b520f25b85
- 出典データセット
- uspto-grants-2013_09
- 特許番号
- US08541425B2
関連ノート
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