Sodium hydride → 1H-Pyrrolo[2,3-b]pyridine-3-carbonitrile, 4-chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]-

HRID 1522006ノート

反応式

HRID 1522006 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[C:10]([C:11]#[N:12])[C:3]=12.[H-].[Na+].Cl[CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21]>O1CCCC1.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:9]=[C:10]([C:11]#[N:12])[C:3]=12

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 457903004-Chloro-1H-pyrrolo[2,3-B]pyridine-3-carbonitrile

生成物 1

HCID 591458241H-Pyrrolo[2,3-b]pyridine-3-carbonitrile, 4-chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]-

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

A solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (2.5 g, 14.08 mmol) in tetrahydrofuran (200 mL) was cooled to 0° C. and treated with sodium hydride (0.5 g, 21.1 mmol). The mixture was stirred at 0° C. for 30 minutes and (2-(chloromethoxy)ethyl)trimethylsilane (2.8 g, 16.9 mmol) was added. After stirring at room temperature for 2 hours, the mixture was treated with brine and extracted with ethyl acetate (three times) and the organic layers were dried over sodium sulfate. Filtration, concentration and purification by flash chromatography (Combi Flash Rf) (silica gel, 40% ethyl acetate in hexane) afforded the title compound. MS (ESI+) m/z 308 (M+H)+.

後処理

  1. stirringAfter stirring at room temperature for 2 hours
  2. extractionextracted with ethyl acetate (three times)
  3. dry with materialthe organic layers were dried over sodium sulfate
  4. filtrationFiltration, concentration and purification by flash chromatography (Combi Flash Rf) (silica gel, 40% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-3e83688e3da144d28d5dc9fe9352a3ea
出典データセット
uspto-grants-2015_07
特許番号
US09073922B2

反応ノート

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