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

HRID 2396499노트

반응식

HRID 2396499 반응식
[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]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 108221371-(Bromoacetyl)piperidineHCID 178480138HCID 178480138, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-5ef0fc615ed047b9baf1921a30cb120c
출처 데이터셋
uspto-grants-1996_02
특허 번호
US05492919

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