Ethylene Glycol → 5-(1,3-Dioxolan-2-yl)-3-iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole

HRID 1038384ノート

反応式

HRID 1038384 の反応式
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]=[O:12])[CH:9]=2)[N:4]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:3]=1.[CH2:21](O)[CH2:22][OH:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:12]1[CH2:21][CH2:22][O:23][CH:11]1[C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:3]=[C:2]2[I:1]

参加物

5

反応物 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 584075833-Iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole-5-carbaldehyde

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

6.11 g (15.2 mmol) 3-iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole-5-carbaldehyde (Example 5A), 2.82 g (45.6 mmol) ethylene glycol and a trace amount of p-toluene sulfonic acid in toluene (100 ml) were heated to reflux overnight using a Dean-Stark trap. After cooling, the mixture was extracted twice with saturated aqueous sodium bicarbonate solution and washed with brine. The organic layer was dried with sodium sulfate, filtered and evaporated to dryness. The remaining substance was purified by preparative RP-HPLC (acetonitrile/water gradient) yielding 3.94 g (58% of th.) of the pure title compound.

後処理

  1. temperatureto reflux overnight
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted twice with saturated aqueous sodium bicarbonate solution
  4. washwashed with brine
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe remaining substance was purified by preparative RP-HPLC (acetonitrile/water gradient)

出典と根拠

ORDレコード
ord-6ea1fa3b460e4ad9ab905f230403ce97
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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