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

HRID 2399518Notes

Reaction equation

HRID 2399518 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.[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1)([O-:16])=[O:15].N#N>CN(C=O)C.C(Cl)Cl>[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:21][C:20]3[CH:23]=[CH:24][C:17]([N+:14]([O-:16])=[O:15])=[CH:18][CH:19]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:13])[CH:3]=1

Participants

6

Reactant 3

HCID 947NitrogenHCID 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-2-ethylimidazo[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 NaB. 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 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. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated to a yellow oil
  4. customchromatographed with 50% ethyl acetate/hexane
  5. additionThe product containing fractions
  6. concentrationconcentrated to a yellow oil which
  7. customcrystallized

Sources & evidence

ORD record
ord-7697ebece1fe4caab77bacab2cf7bd0e
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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