N-Piperidinoethanol → 5-(1,3-Dioxolan-2-yl)-3-[2-(piperidin-1-yl)ethoxy]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole

HRID 1038394노트

반응식

HRID 1038394 반응식
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:10]=[C:9]2I.[N:24]1([CH2:30][CH2:31][OH:32])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C1(C)C=CC=CC=1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:10]=[C:9]2[O:32][CH2:31][CH2:30][N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

참가 물질

4

반응물 2

HCID 18232N-PiperidinoethanolHCID 584076045-(1,3-Dioxolan-2-yl)-3-iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole

생성물 1

HCID 584075815-(1,3-Dioxolan-2-yl)-3-[2-(piperidin-1-yl)ethoxy]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

The title compound was prepared from 600 mg (1.344 mmol) 5-(1,3-dioxolan-2-yl)-3-iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole (Example 6A) in analogy to the procedure described in Example 21A. The procedure was modified by using 5 equivalents of 2-(piperidin-1-yl)ethanol as the alcohol reactant and by switching to toluene as solvent. Instead of using microwave irradiation, the reaction mixture was refluxed for 5 days employing conventional heating. During this time, the same amounts of catalyst and ligand were added again on day 3. The crude product thus obtained was purified by chromatography on silica gel (cyclohexane/ethyl acetate gradient) to afford 244 mg (32% of th.) of the title compound.

후처리

  1. custommicrowave irradiation
  2. temperaturethe reaction mixture was refluxed for 5 days
  3. additionDuring this time, the same amounts of catalyst and ligand were added again on day 3
  4. customThe crude product thus obtained

출처 및 근거

ORD 기록
ord-373c9e526a4f471799039e06becd8ab9
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551989B2

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