Nitrogen → 2-ethyl-5,7-dimethyl-3-(4-nitrobenzyl)-3H-imidazo[4,5-b]pyridine

HRID 1492609Notes

Reaction equation

HRID 1492609 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+].[N+:16]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1)([O-:18])=[O:17].N#N>CN(C=O)C.C(Cl)Cl>[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:23][C:22]3[CH:25]=[CH:26][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:13])[CH:3]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 98153742,6-Dimethyl-8-ethyl-1-deazapurine

Product 1

HCID 104031282-ethyl-5,7-dimethyl-3-(4-nitrobenzyl)-3H-imidazo[4,5-b]pyridineYield 76.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.0 g (1.0 eq, 28.6 mmol) 5,7-dimethyl-2ethylimidazo[4,5-b]pyridine in 30 mL DMF under N2 at rt was added 1.37 g (1.2 eq, 34.3 mmol) of a 60% oil dispersion of NaH. After stirring for 5 minutes, 8.64 g (1.4 eq, 40.0 mmol) of p-nitrobenzyl bromide was added. The dark brown mixture was stirred for 2 hours under a blanket of N2 at rt. The mixture was diluted with 1 L CH2Cl2 and washed with 500 mL H2O and 500 mL saturated aqueous NaCl. The organic phase was dried is over MgSO4 and concentrated to a yellow oil. The oil was flash chromatographed with 50% ethyl acetate/hexane. The product-containing fractions were combined and concentrated to a yellow oil which crystallized on standing, yielding 6.81 g (76.8%) of the title compound.

Workup

  1. washwashed with 500 mL H2O and 500 mL saturated aqueous NaCl
  2. customThe organic phase was dried
  3. concentrationconcentrated to a yellow oil
  4. customchromatographed with 50% ethyl acetate/hexane
  5. concentrationconcentrated to a yellow oil which
  6. customcrystallized

Sources & evidence

ORD record
ord-5fcca0b81515464289530ba2f112e1d4
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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