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

HRID 1038394ノート

反応式

HRID 1038394 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-373c9e526a4f471799039e06becd8ab9
出典データセット
uspto-grants-2013_10
特許番号
US08551989B2

反応ノート

読み込み中…