Sodium hydride → HCID 86757072, compound

HRID 1069597Notes

Reaction equation

HRID 1069597 reaction equation
[CH2:1]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=2)[C:9]([CH2:17][C:18]([NH2:20])=[O:19])=[C:8]1[CH3:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].Br[CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>CN(C=O)C.O>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][O:16][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:8]([CH3:21])=[C:9]2[CH2:17][C:18]([NH2:20])=[O:19])[CH3:32]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 21191844HCID 21191844, compound

Product 1

HCID 86757072HCID 86757072, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-Hexyl-5-hydroxy-2-methyl-1H-indole-3-acetamide (230 mg, 0.8 mmol) was dissolved in 10 mL of DMF and 26 mg (0.8 mmol) of 60% NaH/mineral oil added. The mixture was stirred for 1 hour, 0.115 mL (0.8 mmol) of ethyl 4-bromobutyrate added and stirring continued for 96 hours. The mixture was diluted with water, extracted with ethyl acetate, the ethyl acetate washed with water and dried (Na2SO4). The solution was concentrated at reduced pressure and the residue chromatographed on silica gel (eluted with 3% MeOH/methylene chloride) to give 170 mg (53% yield of [4-[[3-(2-amino-2-oxoethyl)-1-hexyl-2-methyl-1-H-indol-5-yl]oxy]butanoic acid ethyl ester, mp, 69-71° C.

Workup

  1. stirringstirring
  2. waitcontinued for 96 hours
  3. extractionextracted with ethyl acetate
  4. washthe ethyl acetate washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationThe solution was concentrated at reduced pressure
  7. customthe residue chromatographed on silica gel (eluted with 3% MeOH/methylene chloride)

Sources & evidence

ORD record
ord-71c32baf1bb2420789e6cf43f3a7d162
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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