Iodo benzene diacetate → 2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-6-fluoro-8-(triisopropylsilyloxy)quinoline
反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][Si:13]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[CH:11]=1)[N:8]=[C:7]([CH:23]=[N:24][NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[CH:6]=[CH:5]2.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>ClCCl>[N:25]1[N:24]=[C:23]([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[C:10]([O:12][Si:13]([CH:20]([CH3:21])[CH3:22])([CH:17]([CH3:18])[CH3:19])[CH:14]([CH3:15])[CH3:16])[CH:11]=[C:2]([F:1])[CH:3]=3)[N:8]=2)[N:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=12参加物
4
実験手順
6-Fluoro-2-((2-(pyridin-2-yl)hydrazono)methyl)-8-(triisopropylsilyloxy)quinoline (10 g, 23 mmol) was weighed into a 1000 mL 1 neck round bottom flask, followed by addition of iodo benzene diacetate (8.1 g, 25 mmol) and 400 mL of dichloromethane. The mixture was stirred at ambient temperature for 24 hours, at which time the reaction was complete. The crude mixture was partitioned with Na2S2O3, back extracted with DCM, and the combined organics were washed with brine and dried over sodium sulfate, then concentrated in vacuo. The crude product was the purified by flash column chromatography (SP1 Biotage Horizon, 1-15% MeOH/DCM gradient elution), affording the desired product (9.4 g, 94% yield) as a white powder.
後処理
- customThe crude mixture was partitioned with Na2S2O3
- extractionback extracted with DCM
- washthe combined organics were washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- custompurified by flash column chromatography (SP1 Biotage Horizon, 1-15% MeOH/DCM gradient elution)
出典と根拠
- ORDレコード
- ord-8020b346a412429db9e3a7aa6bd4e66e
- 出典データセット
- uspto-grants-2013_11
- 特許番号
- US08575145B2
反応ノート
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