Water → 1-(5-Methoxycarbonylpentyl)-2-(1-imidazolyl)-3-methylindole

HRID 1903408

Reaction equation

HRID 1903408 reaction equation
[H-].[Na+].[N:3]1([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH3:17])=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:7]=[CH:6][N:5]=[CH:4]1.Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25].O>CN(C)C=O>[CH3:27][O:26][C:24]([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]([CH3:17])=[C:8]1[N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 4170292Methyl 6-BromohexanoateHCID 132808392-(1-Imidazolyl)-3-methylindole

Product 1

HCID 132808401-(5-Methoxycarbonylpentyl)-2-(1-imidazolyl)-3-methylindole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 60% sodium hydride (0.34 g) in dimethylformamide (10 ml), while stirring under nitrogen at 0°-5°, is added dropwise a solution of 2-(1-imidazolyl)-3-methyl-indole (1.50 g) in dimethylformamide (15 ml). Upon complete addition the mixture is stirred at 0°-5° for 1 hr. To the nearly complete solution is added methyl 6-bromohexanoate (1.67 g) dropwise. The mixture is stirred at 0°-5° for 0.5 hr, then for two days at room temperature. The solution is poured into water (100 ml) and extracted with ethyl acetate (3×50 ml), dried (MgSO4), filtered, and concentrated in vacuo to give an amber oil which is stirred with 100 ml of petroleum ether for 15 minutes. The mixture is placed in a separatory funnel and the insoluble amber oil separated and removed. The oil is dried in vacuo to give 1-(5-methoxycarbonylpentyl)-2-(1-imidazolyl)-3-methylindole as an oil; NMR (CDCl3): δ3.60(3H), 3.90(2H).

Workup

  1. additionUpon complete addition the mixture
  2. stirringis stirred at 0°-5° for 1 hr
  3. stirringThe mixture is stirred at 0°-5° for 0.5 hr
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give an amber oil which
  9. customThe mixture is placed in a separatory funnel
  10. customthe insoluble amber oil separated
  11. customremoved
  12. customThe oil is dried in vacuo

Sources & evidence

ORD record
ord-b82cddcdb47e43ef875f2fe794b0b687
Source dataset
uspto-grants-1984_03
Patent number
US04436746

Linked notes

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