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

HRID 1522006노트

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HRID 1522006 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

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온도
0 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-3e83688e3da144d28d5dc9fe9352a3ea
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073922B2

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