6-Bromohexanoic acid → HCID 20268202, compound

HRID 1719385Notes

Reaction equation

HRID 1719385 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1)=[C:5]2[CH3:16].[H-].[Na+].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26]>CN(C)C=O.O>[ClH:1].[C:25]([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[C:5]([CH3:16])=[C:6]1[N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1)([OH:27])=[O:26]

Participants

6

Reactant 3

HCID 202106-Bromohexanoic acidHCID 24758Sodium hydrideHCID 13491437HCID 13491437, compound

Product 1

HCID 20268202HCID 20268202, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

A solution of 5-chloro-2-(1-imidazolyl)-3-methylindole (0.37 g) in anhydrous dimethylformamide (4 ml is added dropwise to a suspension of a 50% dispersion of sodium hydride in mineral oil (0.17 g) in anhydrous dimethylformamide (3 ml) while stirring under nitrogen at 0°. The mixture is stirred at 0° for 1/2 hour. To the suspension is then added a solution of 6-bromohexanoic acid (0.35 g) in anhydrous dimethylformamide (4 ml) dropwise. The reaction mixture is stirred at 0° for 1/2 hour and then at room temperature for several hours. The resulting suspension is diluted with water (30 ml) and washed with ether (2×15 ml). The aqueous solution is acidified to pH 5 with 1N hydrochloric acid and extracted with ether (3×30 ml). The extract is dried over magnesium sulfate, filtered and concentrated in vacuo to give an oil which crystallizes. This material is dissolved in ethanol (3 ml) and the solution is treated with 0.11 ml of 7N ethanolic hydrogen chloride. The solution is concentrated in vacuo and the residue is triturated with ether. The hydrochloride salt is collected and is purified by recrystallization from acetonitrile/ether to give 1-(5-carboxypentyl)-5-chloro-2-(1-imidazolyl)-3-methylindole hydrochloride, m.p. 149°-152°.

Workup

  1. stirringThe mixture is stirred at 0° for 1/2 hour
  2. stirringThe reaction mixture is stirred at 0° for 1/2 hour
  3. waitat room temperature for several hours
  4. washwashed with ether (2×15 ml)
  5. extractionextracted with ether (3×30 ml)
  6. dry with materialThe extract is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give an oil which
  10. customcrystallizes
  11. dissolutionThis material is dissolved in ethanol (3 ml)
  12. additionthe solution is treated with 0.11 ml of 7N ethanolic hydrogen chloride
  13. concentrationThe solution is concentrated in vacuo
  14. customthe residue is triturated with ether
  15. customThe hydrochloride salt is collected
  16. customis purified by recrystallization from acetonitrile/ether

Sources & evidence

ORD record
ord-8cf9e5464d864f1ab134b0d0cb05cf37
Source dataset
uspto-grants-1985_09
Patent number
US04539410

Reaction notes

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