Sodium hydride → 7-Methyl-3-[(2'-nitrobiphen-4-yl)methyl]-2-propyl-3H-imidazo[4,5-b]pyridine

HRID 1729427Notes

Reaction equation

HRID 1729427 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([CH2:11][CH2:12][CH3:13])=[N:10][C:3]=12.[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[CH:7]=[CH:6][N:5]=[C:4]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][CH2:12][CH3:13])=[N:10][C:3]=12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 117790721,1'-Biphenyl, 4'-(bromomethyl)-2-nitro-HCID 150208527-Methyl-2-propyl-1H-imidazo[4,5-b]pyridine

Product 1

HCID 1317172477-Methyl-3-[(2'-nitrobiphen-4-yl)methyl]-2-propyl-3H-imidazo[4,5-b]pyridineYield 50.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.913 g (5.2 mmol) of 7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine in 10 mL of anhydrous dimethylformamide was added 0.210 g (5.7 mmol) of a 60% mineral oil dispersion of sodium hydride. The reaction mixture was magnetically stirred under a nitrogen atmosphere for 2 hours, at which point 1.675 g (5.7 mmol) of 4-bromomethyl-2'-nitrobiphenyl was added as a solid. The reaction mixture was stirred an additional 1 hour 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 75% ethyl acetate-hexane, which after evaporation of the pure fractions and drying in vacuo afforded 1.009 g (50%) of the product as a tan solid: NMR (CDCl3) δ 0.97 (t, J=8 Hz, 3H), 1.70-1.83 (m, 2H), 2.66 (s, 3H), 2.81 (t, J=10 Hz, 2H), 5.52 (s, 2H), 7.02 (d, J=6 Hz, 1H), 7.14-7.25 (m, 4H), 7.36 (d, J=10 Hz, 1H), 7.42-7.48 (m, 1H), 7.56-7.61 (m, 1H), 7.82 (d, J=10 Hz, 1H), 8.20 (d, J=6 Hz, 1H); MS (FAB) m/e 387 (MH+).

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 75% ethyl acetate-hexane, which
  10. customafter evaporation of the pure fractions
  11. customdrying in vacuo

Sources & evidence

ORD record
ord-c0a4409c733a4f88b31bebb35cf4843c
Source dataset
uspto-grants-1994_07
Patent number
US05332744

Reaction notes

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