Sodium hydride → 1-(5-Methoxycarbonylpentyl)-5-chloro-3-methyl-2-(3-pyridyl)indole

HRID 1462620Notes

Reaction equation

HRID 1462620 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)=[C:7]2[CH3:19].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27]>CN(C)C=O>[CH3:29][O:28][C:26]([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][N:9]1[C:10]2[C:6](=[CH:5][C:4]([Cl:3])=[CH:12][CH:11]=2)[C:7]([CH3:19])=[C:8]1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)=[O:27]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 4170292Methyl 6-BromohexanoateHCID 212606465-Chloro-3-methyl-2-(3-pyridyl)indole

Product 1

HCID 133621091-(5-Methoxycarbonylpentyl)-5-chloro-3-methyl-2-(3-pyridyl)indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of 1.39 g of a 50% sodium hydride suspension in mineral oil dissolved in 30 ml of dimethylformamide was added under nitrogen at 0°-5° dropwise while stirring a solution of 6.59 g of 5-chloro-3-methyl-2-(3-pyridyl)indole (prepared as described in U.S. Pat. No. 3,468,894) in 60 ml of dimethylformamide. After addition was complete the suspension was stirred at 0° for 1/2 hour. While maintaining the temperature at 0° a solution of 6.06 g of methyl 6-bromohexanoate in 10 ml of dimethylformamide was added dropwise. The reaction mixture was allowed to reach room temperature and was stirred at room temperature for 5 hours, and poured into 400 ml of ice water. The resulting mixture was extracted with ethyl acetate (3×300 ml). The ethyl acetate extract was washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated to dryness to give 1-(5-methoxycarbonylpentyl)-5-chloro-3-methyl-2-(3-pyridyl)indole as an oil.

Workup

  1. additionwas added under nitrogen at 0°-5° dropwise
  2. customprepared
  3. additionAfter addition
  4. additionwas added dropwise
  5. customto reach room temperature
  6. stirringwas stirred at room temperature for 5 hours
  7. extractionThe resulting mixture was extracted with ethyl acetate (3×300 ml)
  8. extractionThe ethyl acetate extract
  9. washwas washed with saturated sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-40e5743973b545c0a686cdb8e1431573
Source dataset
uspto-grants-1984_07
Patent number
US04460777

Reaction notes

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