Indole → HCID 14819382、化合物

HRID 751342ノート

反応式

HRID 751342 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[C:11]1[CH:15]=[CH:14][S:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O>O>[S:13]1[CH:14]=[CH:15][C:11]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[CH:12]1

参加物

6

反応物 4

HCID 798IndoleHCID 11430Potassium CarbonateHCID 133833-BromothiopheneHCID 13387N-methyl-2-pyrrolidone

生成物 1

HCID 14819382HCID 14819382、化合物収率 64.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
180 °C

実験手順

A mixture of indole (5.64 g, 48.3 mmol), 3-bromothiophene (4.84 mL, 51.6 mmol), potassium carbonate (7.16 g, 51.6 mmol), cuprous bromide (298 mg, 2.1 mmol) and N-methylpyrrolidinone (57 mL) is stirred at 180° C. under nitrogen atmosphere for 48 hr. After cooling to room temperature, the reaction mixture is poured into water (300 mL) and then extracted with ethyl acetate. The extract is washed with water, with brine, dried, filtered and concentrated to give a brown oil that is purified by chromatography eluting with heptane-10% dichloromethane. Product containing fraction are combined and concentrated to afford 1-(thien-3-yl)-1H-indole (6.20 g, 64% yield) as a colorless oil.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water, with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a brown oil that
  8. customis purified by chromatography
  9. washeluting with heptane-10% dichloromethane
  10. additionProduct containing fraction
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-2a724582f5c943998424433c6aa46841
出典データセット
uspto-grants-2008_07
特許番号
US07405300B2

反応ノート

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