Sodium hydride → HCID 10833976, compound

HRID 650575Notes

Reaction equation

HRID 650575 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[C:16]3[C:11](=[C:12]([OH:17])[CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[CH3:18])[CH:2]=1.Br[CH2:26][C:27]([O:29][CH3:30])=[O:28].[H-].[Na+]>CN(C=O)C.O>[CH3:30][O:29][C:27](=[O:28])[CH2:26][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[CH:10]=[C:9]([CH3:18])[N:8]2[CH2:7][C:3]1[CH:2]=[C:1]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 10495408HCID 10495408, compound

Product 1

HCID 10833976HCID 10833976, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-((1,1′-Biphenyl)-3-ylmethyl)-4-hydroxy-2-methyl-1H-indole (1030 mg, 3.3 mmol) is alkylated by treating with 0.31 mL (3.3 mmol) of methyl bromoacetate and 132 mg (3.3 mmol) and 132 mg (3.3 mmol) of 60% NaH/mineral oil in DMF and stirring maintained for about 17 hours. The mixture is diluted with water and extracted with ethyl acetate. The ethyl acetate solution is washed with brine, dried (MgSO4), and concentrated at reduced pressure. The product is purified by chromatography over silica gel eluting with 20% EtOAc/hexane, to give 1000 mg (79% yield) of ((1-((1,1′-biphenyl)-3-ylmethyl)-2-methyl-1H-indol-4-yl)oxy)acetic acid methyl ester; mp 99°-102° C.

Workup

  1. temperaturemaintained for about 17 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate solution is washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated at reduced pressure
  6. customThe product is purified by chromatography over silica gel eluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-90afbf5c476749189c9ccb73d2164727
Source dataset
uspto-grants-2001_08
Patent number
US06274616B1

Reaction notes

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