Sodium hydride → (Z)-3-[(4-(2-carbomethoxy-2-phenylethen-1-yl)phenyl)methyl]-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine

HRID 2255562Notes

Reaction equation

HRID 2255562 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3=[N:14][CH:15]=[CH:16][C:17]([CH3:18])=[C:12]3[N:11]=[C:10]2[CH2:19][CH2:20][CH3:21])=[CH:4][CH:3]=1.[H-].[Na+].BrCC1C=CC(/[CH:32]=[C:33](/[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)\[C:34]([O:36][CH3:37])=[O:35])=CC=1>CN(C=O)C>[C:34](/[C:33](/[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[CH:32]\[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3=[N:14][CH:15]=[CH:16][C:17]([CH3:18])=[C:12]3[N:11]=[C:10]2[CH2:19][CH2:20][CH3:21])=[CH:4][CH:3]=1)([O:36][CH3:37])=[O:35]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 193856433-(4-hydroxyphenyl)methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridineHCID 86747178methyl (Z)-3-(4-bromomethylphenyl)-2-phenylpropenoate

Product 1

HCID 67855036(Z)-3-[(4-(2-carbomethoxy-2-phenylethen-1-yl)phenyl)methyl]-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridineYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 30 mg (0.171 mmol) of 2-propyl-7-methylimidazo[4,5-b]pyridine (Example 2, Step D) dissolved in 1 mL of dry DMF was added 11 mg of a 60% oil dispersion of NaH (1.5 eq) and the reaction mixture was stirred under an N2 atmosphere. After stirring at room temperature for 30 minutes the product from Step C (27.4 mg, 0.082 mmol) dissolved in 0.5 mL DMF was added via syringe. The reaction mixture was quenched with saturated NH4Cl solution, and the solvent was removed under in vacuo. The residue was dissolved in EtOAc and washed with H2O and brine. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 50% ethyl acetate/hexane to provide 13.2 mg (38%) of the title compound.

Workup

  1. additionwas added via syringe
  2. customThe reaction mixture was quenched with saturated NH4Cl solution
  3. customthe solvent was removed under in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with H2O and brine
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified on a silica gel flash chromatography column
  10. washeluted with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-7670d0db7c944a9184d96049b42ad158
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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