6-Bromohexanoic acid → 1-(5-Carboxypentyl)-5-methoxy-3-methylindole

HRID 1719382Notes

Reaction equation

HRID 1719382 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](N1C=CN=C1)=[C:6]2[CH3:17].[H-].[Na+].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27]>CN(C)C=O.O>[C:26]([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[C:6]([CH3:17])=[CH:7]1)([OH:28])=[O:27]

Participants

6

Reactant 3

HCID 202106-Bromohexanoic acidHCID 24758Sodium hydrideHCID 20268173HCID 20268173, compound

Product 1

HCID 134914341-(5-Carboxypentyl)-5-methoxy-3-methylindole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

A solution of 5-methoxy-3-methyl-2-(1-imidazolyl)indole (0.57 g) in dimethylformamide (4 ml) is added dropwise to a suspension of sodium hydride (50% dispersion in mineral oil), 0.27 g in dimethylformamide (5 ml) while stirring under N2 at 0°-5°. The mixture is stirred at 5° for 1/2 hour. A solution of 6-bromohexanoic acid (0.55 g) in dimethylformamide (4 ml) is added dropwise to the reaction mixture while stirring at 0°-5°. The mixture is stirred at 0°-5° for 1/2 hour and then overnight at room temperature. The thick suspension is diluted with water (50 ml) and the mixture is washed with ether (2×25 ml). The aqueous layer is acidified to pH 5.6 with 1N hydrochloric acid and extracted with ethyl acetate (3×30 ml). The organic extract is dried over magnesium sulfate, filtered, and concentrated in vacuo to give an oil which becomes partially crystalline. This material is triturated with ether and the solid is collected to give 1-(5-carboxypentyl)-5-methoxy-3-methylindole, m.p. 134°-137°.

Workup

  1. stirringThe mixture is stirred at 5° for 1/2 hour
  2. stirringwhile stirring at 0°-5°
  3. stirringThe mixture is stirred at 0°-5° for 1/2 hour
  4. customovernight
  5. customat room temperature
  6. washthe mixture is washed with ether (2×25 ml)
  7. extractionextracted with ethyl acetate (3×30 ml)
  8. extractionThe organic extract
  9. dry with materialis dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto give an oil which
  13. customThis material is triturated with ether
  14. customthe solid is collected

Sources & evidence

ORD record
ord-b893a39d484f49958508f31f66686612
Source dataset
uspto-grants-1985_09
Patent number
US04539410

Reaction notes

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