Sodium hydride → 3-[4-(1-carbomethoxy-1-(3-chlorophenyl)methoxy)-3-chloro-5-propylphenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo-[4,5-b]pyridine

HRID 1492643Notes

Reaction equation

HRID 1492643 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+].[Cl:16][C:17]1[CH:35]=[C:34]([CH2:36]O)[CH:33]=[C:32]([CH2:38][CH2:39][CH3:40])[C:18]=1[O:19][CH:20]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=1)[C:21]([O:23][CH3:24])=[O:22]>CN(C=O)C>[C:21]([CH:20]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=1)[O:19][C:18]1[C:32]([CH2:38][CH2:39][CH3:40])=[CH:33][C:34]([CH2:36][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:35][C:17]=1[Cl:16])([O:23][CH3:24])=[O:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 98153742,6-Dimethyl-8-ethyl-1-deazapurineHCID 54026416Methyl 2-(2-chloro-4-hydroxymethyl-6-propyl-phenoxy)-2-(3-chlorophenyl)acetate

Product 1

HCID 543926843-[4-(1-carbomethoxy-1-(3-chlorophenyl)methoxy)-3-chloro-5-propylphenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo-[4,5-b]pyridineYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 0.085 g (0.49 mmol) of 5,7-dimethyl-2-ethylimidazo[4,5-b]pyridine in 1.0 mL anhydrous DMF was added 21.0 mg (0.54 mmol) of a 60% oil dispersion of sodium hydride and the reaction mixture was stirred under a nitrogen atmosphere at room temperature for 1 hour. A solution of 0.250 g (0.56 mmol) of the product of Step C in 0.5 mL of DMF was added and the reaction was stirred an additional 2 hours at room temperature. The reaction mixture was partitioned between EtOAc and water, 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 0.150 g (58%) of the title compound.

Workup

  1. stirringthe reaction was stirred an additional 2 hours at room temperature
  2. customThe reaction mixture was partitioned between EtOAc and water
  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-8ec98483b3924366baa035813fa55002
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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