反応式
[C:1]([Si:5]([CH3:24])([CH3:23])[N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:16](=[O:22])[N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)([CH3:4])([CH3:3])[CH3:2].CN(CCN(C)C)C.C([Li])(CC)C.[Cl:38]C(Cl)(Cl)C(Cl)(Cl)Cl.[Cl-].[NH4+]>C1COCC1>[C:1]([Si:5]([CH3:24])([CH3:23])[N:6]1[C:14]2[C:9](=[C:10]([Cl:38])[C:11]([O:15][C:16](=[O:22])[N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)([CH3:2])([CH3:3])[CH3:4]参加物
反応物 5
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- -78 °C
実験手順
Diethyl-carbamic acid 1-(tert-butyl-dimethyl-silanyl)-1H-indol-5-yl ester (9.26 g, 26.7 mmol) is dissolved in THF (250 mL), flushed with nitrogen and cooled to −78° C. TMEDA (5 mL, 33.1 mmol) is then added followed by sec-butyllithium (24.8 mL, 34.7 mmol) and the reaction is stirred for 30 minutes. Hexachloroethane (12.73 g, 53.8 mmol) in 50 mL of THF is added over 10 minutes to the reaction. The reaction is allowed to warm to room temperature overnight (15 hours). The reaction is cooled using an ice bath and a saturated ammonium chloride (aq) solution is added (150 mL). The mixture is then extracted with ethyl acetate, dried (sodium sulfate) and concentrated to obtain the title compound as an oil that is used without further purification. MS (ESI) m/z 381.1 (M+1).
後処理
- customflushed with nitrogen
- temperatureto warm to room temperature overnight (15 hours)
- temperatureThe reaction is cooled
- extractionThe mixture is then extracted with ethyl acetate
- dry with materialdried (sodium sulfate)
- concentrationconcentrated
出典と根拠
- ORDレコード
- ord-1f12c182fb30481e9d63de934582b7f4
- 出典データセット
- uspto-grants-2013_09
- 特許番号
- US08541432B2
関連ノート
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