Indole → HCID 14819382, compound

HRID 1196916Notes

Reaction equation

HRID 1196916 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+].O>CN1CCCC1=O.[Cu](Br)Br>[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

7

Reactant 4

HCID 798IndoleHCID 962WaterHCID 11430Potassium CarbonateHCID 133833-Bromothiophene

Product 1

HCID 14819382HCID 14819382, compound

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of indole (16 g, 0.136 M), 3-bromothiophene (24.75 g, 0.146 M), potassium carbonate (20.1 g, 0.146 M) and copper bromide (0.84 g, 0.003 M) in 160 ml of N-methyl-2-pyrrolidinone was stirred and heated to 180° C. (under nitrogen atmosphere) for 42 hours. After this time, the reaction mixture was poured onto 800 ml of water and extracted with ethyl acetate (2×350 ml). The combined ethyl acetate extracts were washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo leaving a dark brown-black oil. The crude reaction product was chromatographed on a silica gel column with hexane/CH2Cl2 3:1 as eluant. Yield=9.14 g of yellow liquid which was homogeneous by thin layer chromatography. MS: M+ =199.

Workup

  1. extractionextracted with ethyl acetate (2×350 ml)
  2. washThe combined ethyl acetate extracts were washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customleaving a dark brown-black oil
  7. customThe crude reaction product
  8. customwas chromatographed on a silica gel column with hexane/CH2Cl2 3:1 as eluant

Sources & evidence

ORD record
ord-fae868013fca485aaa5fbf36350a3282
Source dataset
uspto-grants-1992_05
Patent number
US05116854

Reaction notes

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