Sodium hydride → HCID 15233569, compound

HRID 466708Notes

Reaction equation

HRID 466708 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:13])[CH:3]=1.[H-].[Na+].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N+:30]([O-:32])=[O:31])=[CH:20][CH:19]=1>CN(C)C=O>[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[N+:30]([O-:32])=[O:31])=[CH:22][CH:23]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:13])[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 117790721,1'-Biphenyl, 4'-(bromomethyl)-2-nitro-HCID 178437439HCID 178437439, compound

Product 1

HCID 15233569HCID 15233569, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.199 g (1.13 mmol) of 5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine in 5 mL of anhydrous dimethylformamide was added 0.050 g (1.25 mmol) of a 60% mineral oil dispersion of sodium hydride. The reaction mixture was magnetically stirred under a nitrogen atmosphere for 30 minutes, at which point 0.365 g (1.25 mmol) of 4-bromomethyl-2'-nitrobiphenyl was added as a solid. The reaction mixture was stirred an additional 1.5 hours at room temperature, then partitioned between ethyl acetate and water. The organic layer was extracted, washed with brine, dried (MgSO4), filtered and evaporated. The residual oil was purified on a silica gel flash chromatography column eluted with 50% ethyl acetate-hexane, which after evaporation of the pure fractions and drying in vacuo afforded 0.340 g (77%) of the product as a tan solid.

Workup

  1. additionwas added as a solid
  2. custompartitioned between ethyl acetate and water
  3. extractionThe organic layer was extracted
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residual oil was purified on a silica gel flash chromatography column
  9. washeluted with 50% ethyl acetate-hexane, which
  10. customafter evaporation of the pure fractions
  11. customdrying in vacuo

Sources & evidence

ORD record
ord-2bb9879106a94526b040eb0b9051f58a
Source dataset
uspto-grants-1992_10
Patent number
US05157026

Reaction notes

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