1-(2-Hydroxyethyl)-1H-pyrazole → 5-(1,3-Dioxolan-2-yl)-3-[2-(1H-pyrazol-1-yl)ethoxy]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole

HRID 1038395ノート

反応式

HRID 1038395 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([CH2:29][CH2:30][OH:31])[CH:28]=[CH:27][CH:26]=[N: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:31][CH2:30][CH2:29][N:24]1[CH:28]=[CH:27][CH:26]=[N:25]1

参加物

4

反応物 2

HCID 2370311-(2-Hydroxyethyl)-1H-pyrazoleHCID 584076045-(1,3-Dioxolan-2-yl)-3-iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole

生成物 1

HCID 584076485-(1,3-Dioxolan-2-yl)-3-[2-(1H-pyrazol-1-yl)ethoxy]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
140 °C

実験手順

The title compound was prepared from 300 mg (0.672 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-(1H-pyrazol-1-yl)-ethanol as the alcohol reactant and by switching to toluene as solvent. The reaction mixture was heated to 140° C. for 2 h using microwave irradiation, after which time the same amounts of catalyst and ligand were added again. This cycle was repeated one more time. The crude product thus obtained was purified by preparative RP-HPLC (acetonitrile/water gradient) to afford 153 mg (52% of th.) of the title compound.

後処理

  1. custommicrowave irradiation
  2. additionafter which time the same amounts of catalyst and ligand were added again
  3. customThe crude product thus obtained

出典と根拠

ORDレコード
ord-25444444e97f4654961443b38a90f509
出典データセット
uspto-grants-2013_10
特許番号
US08551989B2

反応ノート

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