Potassium Hydroxide → 1-[2-(4-Ethoxycarbonylphenoxy)ethyl]-2-(3-pyridyl)-3-methylindole

HRID 1633133Notes

Reaction equation

HRID 1633133 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.[OH-].[K+].Br[CH2:20][CH2:21][O:22][C:23]1[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[CH2:30]([O:29][C:27]([C:26]1[CH:32]=[CH:33][C:23]([O:22][CH2:21][CH2:20][N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]([CH3:1])=[C:3]2[C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:24][CH:25]=1)=[O:28])[CH3:31]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 12708668Ethyl 4-(2-bromoethoxy)benzoateHCID 155913683-Methyl-2-(3-pyridyl)indole

Product 1

HCID 133621101-[2-(4-Ethoxycarbonylphenoxy)ethyl]-2-(3-pyridyl)-3-methylindole

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a mixture of 4.17 g of 3-methyl-2-(3-pyridyl)indole, 0.64 g of tetra-n-butyl ammonium bromide and 1.2 g of powdered KOH in 500 ml of acetonitrile, while stirring at room temperature under nitrogen, is added 5.06 g of ethyl p-(2-bromoethoxy)benzoate [for preparation see U.S. Pat. No. 2,790,825 (1957)]. The suspension is stirred for five days. After filtration to remove KBr, the filtrate is concentrated to an oil which is dissolved in ethyl acetate and extracted with 3 N HCl. The acid layer is separated and treated with 3 N NaOH. This suspension is extracted with ethyl acetate (3×100 ml) and the organic extract is separated, dried over MgSO4, and concentrated to give as an oil 1-[2-(4-ethoxycarbonylphenoxy)ethyl]-2-(3-pyridyl)-3-methylindole.

Workup

  1. customfor preparation
  2. stirringThe suspension is stirred for five days
  3. filtrationAfter filtration
  4. customto remove KBr
  5. concentrationthe filtrate is concentrated to an oil which
  6. dissolutionis dissolved in ethyl acetate
  7. extractionextracted with 3 N HCl
  8. customThe acid layer is separated
  9. additiontreated with 3 N NaOH
  10. extractionThis suspension is extracted with ethyl acetate (3×100 ml)
  11. extractionthe organic extract
  12. customis separated
  13. dry with materialdried over MgSO4
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-acd115ea587f422c894ff9dfa7a44920
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

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