Sodium hydride → 1-[1-Acetylpiperidyl]-3-(1-methyl-1H-indol-3-yl)-1,2,4-triazole

HRID 2396499ノート

反応式

HRID 2396499 の反応式
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[N:15]=[CH:14][NH:13][N:12]=2)=[CH:3]1.[H-].[Na+].Br[CH2:19][C:20]([N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:21]>C1COCC1>[C:20]([N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[N:13]1[CH:14]=[N:15][C:11]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=2)=[N:12]1)(=[O:21])[CH3:19]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 108221371-(Bromoacetyl)piperidineHCID 178480138HCID 178480138、化合物

生成物 1

HCID 543655421-[1-Acetylpiperidyl]-3-(1-methyl-1H-indol-3-yl)-1,2,4-triazole収率 26%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

3-(1-Methyl-1H-indol-3-yl)-1,2,4-triazole (0.190 g, 0.960 mmol) was dissolved with stirring in dry THF (5 ml) and was treated with sodium hydride (80%) (0.032 g, 1.05 mmol), followed by 1-(bromoacetyl)piperidine (Bull. Soc, Chim. Fr. 1964, 5, 1063-9) (0.232 g, 1.05 mmol) in dry THF (1 ml). After 4 h, the reaction mixture was evaporated under reduced pressure and partitioned between EtOAc and water. The organic layer was then dried (Na2SO4) and evaporated under reduced pressure to give a yellow oil, which was purified by silica-gel chromatography (EtOAc→EtOAc:MeOH 100:1 as eluant) to give the title compound (D5b) as a white solid (0.080 g, 26%).

後処理

  1. customthe reaction mixture was evaporated under reduced pressure
  2. custompartitioned between EtOAc and water
  3. dry with materialThe organic layer was then dried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customto give a yellow oil, which
  6. customwas purified by silica-gel chromatography (EtOAc→EtOAc:MeOH 100:1 as eluant)

出典と根拠

ORDレコード
ord-5ef0fc615ed047b9baf1921a30cb120c
出典データセット
uspto-grants-1996_02
特許番号
US05492919

反応ノート

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