Dimethylformamide → Ethyl 1-(methoxymethyl)-7-nitro-5-(trifluoromethoxy)-1H-indole-2-carboxylate

HRID 1851381노트

반응식

HRID 1851381 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([O:18][C:19]([F:22])([F:21])[F:20])[CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9]2)([O-:3])=[O:2].[H-].[Na+].CN(C)C=O.[CH3:30][O:31][CH2:32]Cl>O1CCCC1.C(OCC)(=O)C>[CH3:30][O:31][CH2:32][N:11]1[C:12]2[C:8](=[CH:7][C:6]([O:18][C:19]([F:22])([F:20])[F:21])=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2])[CH:9]=[C:10]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 57476182ethyl 7-nitro-5-(trifluoromethoxy)-1H-indole-2-carboxylate

생성물 1

HCID 57901589Ethyl 1-(methoxymethyl)-7-nitro-5-(trifluoromethoxy)-1H-indole-2-carboxylate수율 74%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
4 °C

실험 절차

A mixture of ethyl 7-nitro-5-(trifluoromethoxy)-1H-indole-2-carboxylate (1.19 g), 60% sodium hydride (0.18 g) and N,N-dimethylformamide (20 mL) was stirred at 4° C. for 20 min. A solution (5 mL) of chloromethyl methyl ether (0.33 mL) in tetrahydrofuran was added dropwise. After stirring at 4° C. for 3 hr, the reaction solution was diluted with ethyl acetate, washed with aqueous citric acid solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=5:95-20:80) to give the title compound (1.0 g, yield 74%) as pale-yellow prism crystals.

후처리

  1. stirringAfter stirring at 4° C. for 3 hr
  2. washwashed with aqueous citric acid solution, water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ae052c4d4623480a8860a0db8fb5bd7a
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957070B2

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