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Sulfuric acid magnesium salt (1:1) → {2-[2-(3,5-dimethylphenyl)-5-methanesulfonyl-1H-indol-3-yl]propyl}-(4-pyridin-4-yl-butyl)amine

HRID 1458370
ノート
印刷プレビュー

反応式

HRID 1458370 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][CH:10]=O)=[CH:3][CH:2]=1.[CH3:12][C:13]1[CH:14]=[C:15]([C:20]2[NH:21][C:22]3[C:27]([C:28]=2[CH:29]([CH3:32])[CH2:30][NH2:31])=[CH:26][C:25]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:24][CH:23]=3)[CH:16]=[C:17]([CH3:19])[CH:18]=1.S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>>[CH3:19][C:17]1[CH:16]=[C:15]([C:20]2[NH:21][C:22]3[C:27]([C:28]=2[CH:29]([CH3:32])[CH2:30][NH:31][CH2:10][CH2:9][CH2:8][CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:26][C:25]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:24][CH:23]=3)[CH:14]=[C:13]([CH3:12])[CH:18]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 114464344-Pyridin-4-ylbutanalHCID 221009152-[2-(3,5-dimethylphenyl)-5-methanesulfonyl-1H-indol-3-yl]propylamine

生成物 1

HCID 22100895{2-[2-(3,5-dimethylphenyl)-5-methanesulfonyl-1H-indol-3-yl]propyl}-(4-pyridin-4-yl-butyl)amine収率 42.2%

反応条件

温度
-5 °C

実験手順

A mixture of 4-pyridin-4-yl-butyraldehyde (23 mg), 2-[2-(3,5-dimethylphenyl)-5-methanesulfonyl-1H-indol-3-yl]propylamine (50 mg) and magnesium sulfate (76 mg) were diluted with 1.5 mL CDCl3 and stirred at -5° C. After 15 minutes, a solution of sodium borohydride (6.8 mg in 1.5 mL dry methanol) were added and the mixture stirred at low temperature for an additional 20 minutes. At this time the reaction was quenched by the addition of water, extracted with ethyl acetate and the organic portion washed sequentially with water and brine then dried over sodium sulfate. Purification of the concentrate by preparative TLC on silica gel (methylene chloride:methanol, 9:1) gave the title compound (29 mg).

後処理

  1. additionwere diluted with 1.5 mL CDCl3
  2. stirringthe mixture stirred at low temperature for an additional 20 minutes
  3. customAt this time the reaction was quenched by the addition of water
  4. extractionextracted with ethyl acetate
  5. washthe organic portion washed sequentially with water and brine
  6. dry with materialthen dried over sodium sulfate
  7. customPurification of the
  8. concentrationconcentrate by preparative TLC on silica gel (methylene chloride:methanol, 9:1)

出典と根拠

ORDレコード
ord-0d3758a6a3f04a7d89192f9dedee5088
出典データセット
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05849764

反応ノート

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