Sodium hydride → 3-[4-(1-Carboxy-1-(3,4-methylenedioxyphenyl)methoxy)-3,5-dichlorophenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine

HRID 1741757Notes

Reaction equation

HRID 1741757 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[N:8]=[C:9]([CH2:11][CH3:12])[NH:10][C:5]2=[C:4]([CH3:13])[CH:3]=1.[H-].[Na+].Br[CH2:17][C:18]1[CH:39]=[C:38]([Cl:40])[C:21]([O:22][CH:23]([C:29]2[CH:34]=[CH:33][C:32]3[O:35][CH2:36][O:37][C:31]=3[CH:30]=2)[C:24]([O:26]CC)=[O:25])=[C:20]([Cl:41])[CH:19]=1>CN(C=O)C>[C:24]([CH:23]([C:29]1[CH:34]=[CH:33][C:32]2[O:35][CH2:36][O:37][C:31]=2[CH:30]=1)[O:22][C:21]1[C:20]([Cl:41])=[CH:19][C:18]([CH2:17][N:8]2[C:6]3=[N:7][C:2]([CH3:1])=[CH:3][C:4]([CH3:13])=[C:5]3[N:10]=[C:9]2[CH2:11][CH3:12])=[CH:39][C:38]=1[Cl:40])([OH:26])=[O:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 98153742,6-Dimethyl-8-ethyl-1-deazapurineHCID 20089189Ethyl 2-(4-bromomethyl-2,6-dichlorophenoxy)-2-(3,4-methylenedioxyphenyl)acetate

Product 1

HCID 190105063-[4-(1-Carboxy-1-(3,4-methylenedioxyphenyl)methoxy)-3,5-dichlorophenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridineYield 76.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 0.034 g (0.20 mmol) of 5,7-dimethyl-2-ethylimidazo[4,5-b]pyridine in 0.5 mL anhydrous DMF was added 8.6 mg (0.22 mmol) of a 60% oil dispersion of sodium hydride and the reaction mixture was stirred under a nitrogen atmosphere at room temperature for 30 minutes. A solution of 0.100 g (0.22 mmol) of the product of Step B in 0.9 mL of DMF was added and the reaction was stirred an additional 1.5 hour at room temperature. The reaction mixture was partitioned between EtOAc and 5% aqueous NH4Cl, separated, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 50% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded 0.081 g (74%) of the title compound.

Workup

  1. stirringthe reaction was stirred an additional 1.5 hour at room temperature
  2. customThe reaction mixture was partitioned between EtOAc and 5% aqueous NH4Cl
  3. customseparated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified on a silica gel flash chromatography column
  8. washeluted with 50% EtOAc-hexane
  9. customEvaporation of the purified fractions
  10. customdrying in vacuo

Sources & evidence

ORD record
ord-da2dfc81a7da4757b69e1e393257ed84
Source dataset
uspto-grants-1994_08
Patent number
US05334598

Reaction notes

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