Indole → HCID 14819382, compound

HRID 1678124Notes

Reaction equation

HRID 1678124 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 14819382HCID 14819382, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d3cd657940bf4fc6b4986eb95803c9b0
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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