Water → 5-chloro-1-(3-methylbenzyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 2242345

反応式

HRID 2242345 の反応式
[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]([Cl:17])=[CH:12][CH:11]=2)=[O:7])[CH3:4].[CH3:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]Br.O>CN(C=O)C>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH2:18][C:19]2[CH:26]=[CH:25][CH:24]=[C:21]([CH3:22])[CH:20]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([Cl:17])=[CH:12][CH:11]=2)=[O:7])[CH3:4]

参加物

6

反応物 4

HCID 962WaterHCID 12099m-Xylyl bromideHCID 24758Sodium hydrideHCID 78518Ethyl 5-chloroindole-2-carboxylate

生成物 1

HCID 685478555-chloro-1-(3-methylbenzyl)-1H-indole-2-carboxylic acid ethyl ester収率 103.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60% dispersion in mineral oil, 0.44 g, 7.45 mmol) was added to a suspension of 5-chloro-1H-indole-2-carboxylic acid ethyl ester (2.00 g, 8.94 mmol) in N,N′-dimethylformamide (DMF) (20 ml) under nitrogen. The mixture was stirred for 1 h before addition of the 3-methylbenzyl bromide (2.07 g, 2.48 ml) and the reaction stirred for 17.5 h. Water was added to reaction mixture which precipitated product as a gummy solid. Supernatant liquid was decanted and the solid washed with water. The product was dissolved in dichloromethane (DCM), washed with water, dried over magnesium sulfate and concentrated. Purification by silica chromatography using DCM as eluent, yielded 5-chloro-1-(3-methylbenzyl)-1H-indole-2-carboxylic acid ethyl ester (3.03 g, 95%).

後処理

  1. customprecipitated product as a gummy solid
  2. customSupernatant liquid was decanted
  3. washthe solid washed with water
  4. dissolutionThe product was dissolved in dichloromethane (DCM)
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customPurification by silica chromatography

出典と根拠

ORDレコード
ord-c1f57a0000224535a27cfb3c1c0427c4
出典データセット
uspto-grants-2010_03
特許番号
US07671080B2

関連ノート

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