Hydrochloric Acid → 5-bromo-6-methyl-1H-indole

HRID 1754962ノート

反応式

HRID 1754962 の反応式
COC(=O)[NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([Br:12])=[CH:7][C:6]=1[C:13]#[C:14][Si](C)(C)C.[O-]CC.[Na+].Cl>C(O)C.[Cl-].[Na+].O>[Br:12][C:8]1[CH:7]=[C:6]2[C:5](=[CH:10][C:9]=1[CH3:11])[NH:4][CH:14]=[CH:13]2

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 66816224(4-Bromo-5-methyl-2-trimethylsilanylethynyl-phenyl)-carbamic acid methyl ester

生成物 1

HCID 247292415-bromo-6-methyl-1H-indole収率 66.1%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
70 °C

実験手順

(4-Bromo-5-methyl-2-trimethylsilanylethynyl-phenyl)-carbamic acid methyl ester (506 mg, 1.49 mmol) was dissolved in ethanol (6 ml). Sodium ethoxide (20% solution in ethanol, 1.17 ml, 2.97 mmol) was added and the mixture was stirred at 70° C. overnight. The reaction solution was poured into ice water, and 1 N hydrochloric acid and saturated brine were added to this mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to give 5-bromo-6-methyl-1H-indole (207 mg, 66%).

後処理

  1. additionwere added to this mixture
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-ffee61e408fd43899e86637587047854
出典データセット
uspto-grants-2015_10
特許番号
US09169254B2

反応ノート

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