Sodium hydride → HCID 10764229, compound

HRID 1069606

Reaction equation

HRID 1069606 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][C:7]=1[CH3:17])[CH3:2].[H-].[Na+].Br[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:7]=1[CH3:17])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2633651-(Bromomethyl)-2-phenylbenzeneHCID 10729163Ethyl (5-methoxy-2-methyl-1H-indol-3-yl)acetate

Product 1

HCID 10764229HCID 10764229, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-([1,11′-Biphenyl]-2-ylmethyl)-5-methoxy,y-2-methyl-1H-indole-3-acetic acid ethyl ester. 5-Methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester (988 mg, 4 mmol) was added to 160 mg (4 mmol) of NaH/mineral oil (previously washed with hexane), the mixture stirred for 0.5 hours and 0.74 mL (4 mmol) of2- (bromomethyl) biphenyl added. After 2 hours, water was added and the mixture extracted with ethyl acetate. The ethyl acetate was washed with brine, dried (MgSO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel eluting with 20% EtOAc/hexane to give 1.18 g (72% yield) of 1-([1,1′-biphenyl]-2-ylmethyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester as an oil.

Workup

  1. washpreviously washed with hexane), the mixture
  2. waitAfter 2 hours
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe ethyl acetate was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-7116ac58940b4af186b494fa8da01608
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Linked notes

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