Sodium hydride → HCID 70032910, 화합물

HRID 434020

반응식

HRID 434020 반응식
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([O:17][CH2:18][CH:19]=[CH2:20])=[CH:12][CH:11]=2)=[O:7])[CH3:4].[CH2:21]1[O:25][C:24]2[CH:26]=[C:27]([Cl:32])[C:28]([CH2:30]Cl)=[CH:29][C:23]=2[O:22]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH2:30][C:28]2[C:27]([Cl:32])=[CH:26][C:24]3[O:25][CH2:21][O:22][C:23]=3[CH:29]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([O:17][CH2:18][CH:19]=[CH2:20])=[CH:12][CH:11]=2)=[O:7])[CH3:4]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 901136-Chloropiperonyl chlorideHCID 13286893Ethyl 5-[(prop-2-en-1-yl)oxy]-1H-indole-2-carboxylate

생성물 1

HCID 70032910HCID 70032910, 화합물수율 43%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of NaH (60% suspension in mineral oil, 0.24 g, 6.12 mmol) and DMF (20 mL) was added 5-allyloxyindole-2-carboxylic acid ethyl ester (1.0 g, 4.08 mmol), from Example 1(d). After stirring at room temperature for 1 h, 6-chloropiperonyl chloride (0.84 g, 4.08 mmol) was added followed by the addition of tetrabutyl ammonium iodide (0.15 g, 0.41 mmol). The reaction was stirred at room temperature for 18 h. When the reaction was complete as indicated by TLC, the reaction mixture was partitioned between EtOAc and water. The organic layer was washed with brine and dried (Na2SO4). The solvent was removed in vacuo and the resulting crude product was purified by flash column chromatography (silica gel, EtOAc/hexanes) to yield the desired product as an oil (0.72 g, 43%). LC/MS (ES+) m/e 414.0 [M+H]+.

후처리

  1. stirringThe reaction was stirred at room temperature for 18 h
  2. customthe reaction mixture was partitioned between EtOAc and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed in vacuo
  6. customthe resulting crude product was purified by flash column chromatography (silica gel, EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-b1232f5cd63a4771b76d4c4fa67413d4
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06670388B1

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