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Ammonium formate → 1-{[3-(4-methoxybenzyl)-2-phenyl-3H-imidazo[4,5-b]pyridin-7-yl]methyl}-4-propylpyrrolidin-2-one

HRID 1924326
ノート
印刷プレビュー

反応式

HRID 1924326 の反応式
[N+:1]([CH2:4][CH:5]([CH2:12][CH2:13][CH3:14])[CH2:6][C:7]([O:9]CC)=O)([O-])=O.C([O-])=O.[NH4+].[CH3:19][O:20][C:21]1[CH:44]=[CH:43][C:24]([CH2:25][N:26]2[C:30]3=[N:31][CH:32]=[CH:33][C:34]([CH:35]=O)=[C:29]3[N:28]=[C:27]2[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:23][CH:22]=1>CO.CCOCC.[Pd]>[CH3:19][O:20][C:21]1[CH:44]=[CH:43][C:24]([CH2:25][N:26]2[C:30]3=[N:31][CH:32]=[CH:33][C:34]([CH2:35][N:1]4[CH2:4][CH:5]([CH2:12][CH2:13][CH3:14])[CH2:6][C:7]4=[O:9])=[C:29]3[N:28]=[C:27]2[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[CH:23][CH:22]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 2723923Ammonium formateHCID 14463324Ethyl 3-(nitromethyl)hexanoateHCID 536291983-(4-methoxybenzyl)-2-phenyl-3H-imidazo[4,5-b]pyridine-7-carbaldehyde

生成物 1

HCID 536291991-{[3-(4-methoxybenzyl)-2-phenyl-3H-imidazo[4,5-b]pyridin-7-yl]methyl}-4-propylpyrrolidin-2-one収率 68.2%

試薬・触媒・溶媒 3

HCID 23938Palladium
触媒
HCID 887Methanol溶媒2 回
HCID 3283Diethyl Ether溶媒

実験手順

Ethyl 3-(nitromethyl)hexanoate (0.52 g, 1.1 eq, 2.55 mmol) is dissolved in absolute methanol (8 ml). Then 10% Pd/C (0.2 g) and ammonium formate (1 g) are added under vigorous stirring. After 15 min, the mixture is diluted with ether (100 ml) and filtered. The solid on the filter is washed with ether (2×50 ml). A solution of 3-(4-methoxybenzyl)-2-phenyl-3H-imidazo[4,5-b]pyridine-7-carbaldehyde x225 (1 g, 1 eq, 2.9 mmol) in methanol (5 ml) is added immediately. The combined solution is evaporated in the vacuum of a rotary evaporator. The residue is dissolved in methanol (10 ml), CH(OMe)3 (0.5 ml) is added and the obtained solution is stirred at room temperature for 16 h. An excess of NaBH4 (1 g in several small portions) is then added under vigorous stirring for 20 min. The reaction mixture is evaporated in the vacuum of a rotary evaporator. The residue is partitioned between ethyl acetate and water. The organic phase is separated, dried with anhydrous sodium sulfate, and evaporated. The residue is dissolved in acetonitrile (10 ml), and the solution is refluxed for 24 h to complete the cyclization. The solvent is distilled off. The residue is purified by chromatography on silicagel (CCl4/MeCN) to yield 0.79 g of 1-{[3-(4-methoxybenzyl)-2-phenyl-3H-imidazo[4,5-b]pyridin-7-yl]methyl}-4-propylpyrrolidin-2-one x226.

後処理

  1. filtrationfiltered
  2. washThe solid on the filter is washed with ether (2×50 ml)
  3. customThe combined solution is evaporated in the vacuum of a rotary evaporator
  4. dissolutionThe residue is dissolved in methanol (10 ml)
  5. additionCH(OMe)3 (0.5 ml) is added
  6. additionAn excess of NaBH4 (1 g in several small portions) is then added
  7. stirringunder vigorous stirring for 20 min
  8. customThe reaction mixture is evaporated in the vacuum of a rotary evaporator
  9. customThe residue is partitioned between ethyl acetate and water
  10. customThe organic phase is separated
  11. dry with materialdried with anhydrous sodium sulfate
  12. customevaporated
  13. dissolutionThe residue is dissolved in acetonitrile (10 ml)
  14. temperaturethe solution is refluxed for 24 h
  15. distillationThe solvent is distilled off
  16. customThe residue is purified by chromatography on silicagel (CCl4/MeCN)

出典と根拠

ORDレコード
ord-aed0c53b4f774ae9ad77fbbb34191ac6
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08178533B2

反応ノート

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