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

HRID 1851381ノート

反応式

HRID 1851381 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
4 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ae052c4d4623480a8860a0db8fb5bd7a
出典データセット
uspto-grants-2015_02
特許番号
US08957070B2

反応ノート

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