Sodium hydride → 3-[4-(2-cyano-2-phenylethyl)phenyl]methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine

HRID 2399463Notes

Reaction equation

HRID 2399463 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]=[C:9]([CH2:11][CH2:12][CH3:13])[NH:10][C:3]=12.[H-].[Na+].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:26]#[N:27])=[CH:20][CH:19]=1>CN(C=O)C>[C:26]([CH:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:8]2[C:4]3=[N:5][CH:6]=[CH:7][C:2]([CH3:1])=[C:3]3[N:10]=[C:9]2[CH2:11][CH2:12][CH3:13])=[CH:19][CH:20]=1)#[N:27]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 150208527-Methyl-2-propyl-1H-imidazo[4,5-b]pyridineHCID 193855943-[4-(Bromomethyl)phenyl]2-phenylpropanonitrile

Product 1

HCID 197381193-[4-(2-cyano-2-phenylethyl)phenyl]methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridineYield 19.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 7-methyl-2-propylimidazo [4,5-b]pyridine (106 mg, 0.61 mmol) in DMF (3 mL) was added NaH (0.91 mmol). The suspension was stirred at room temperature for 30 minutes, at which time a solution of the product of Step D (200 mg, 0.667 mmol) in DMF (2 mL) was added. The mixture was stirred for 2 hours at room temperature, quenched with water, and then concentrated in vacuo. The residue was partitioned between water and EtOAc, and the combined organic layers were washed with brine, dried (K2CO3), filtered, and evaporated in vacuo. The residue was chromatographed on a silica gel flash chromatography column eluted with 50% ethyl acetate/hexane to afford 46 mg (19%) of the title compound.

Workup

  1. additionwas added
  2. customquenched with water
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between water and EtOAc
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried (K2CO3)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was chromatographed on a silica gel flash chromatography column
  10. washeluted with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-860a0081b6c543b0bcfc7f4f03a92054
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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