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

HRID 1754962노트

반응식

HRID 1754962 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 247292415-bromo-6-methyl-1H-indole수율 66.1%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
70 °C

실험 절차

(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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-ffee61e408fd43899e86637587047854
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169254B2

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