Acetic Acid → 3-[4-(4-chloro-2-cyano-1-pyrrolyl)benzyl]-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine

HRID 248373Notes

Reaction equation

HRID 248373 reaction equation
[C:1]([N:6]([C:22]1[C:27]([N+:28]([O-])=O)=[C:26]([CH3:31])[CH:25]=[CH:24][N:23]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]2[C:20]#[N:21])=[CH:10][CH:9]=1)(=O)[CH2:2][CH2:3][CH3:4].C(O)(=O)C>[Fe].C(O)C>[Cl:19][C:17]1[CH:16]=[C:15]([C:20]#[N:21])[N:14]([C:11]2[CH:12]=[CH:13][C:8]([CH2:7][N:6]3[C:22]4=[N:23][CH:24]=[CH:25][C:26]([CH3:31])=[C:27]4[N:28]=[C:1]3[CH2:2][CH2:3][CH3:4])=[CH:9][CH:10]=2)[CH:18]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 197595662-[N-butyryl-N-[4-(4-chloro-2-cyano-1-pyrrolyl)benzyl]amino]-4-methyl-3-nitropyridine

Product 1

HCID 197593453-[4-(4-chloro-2-cyano-1-pyrrolyl)benzyl]-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridineYield 90.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-[N-butyryl-N-[4-(4-chloro-2-cyano-1-pyrrolyl)benzyl]amino]-4-methyl-3-nitropyridine (700 mg), iron powder (894 mg), acetic acid (1.8 ml) and ethanol (15 ml) was stirred under reflux for 15 hours. After being cooled to room temperature, the reaction mixture was filtered and the filtrate was evaporated in vacuo. The residue was partitioned into ethyl acetate (100 ml) and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography (n-hexane-ethyl acetate =1:1) to give 3-[4-(4-chloro-2-cyano-1-pyrrolyl)benzyl]-7-methyl-2-propyl-3H-imidazo-[4,5-b]pyridine (565 mg) as a pale yellow powder.

Workup

  1. temperatureunder reflux for 15 hours
  2. filtrationthe reaction mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was partitioned into ethyl acetate (100 ml) and saturated aqueous sodium hydrogencarbonate solution
  5. washThe organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by a silica gel column chromatography (n-hexane-ethyl acetate =1:1)

Sources & evidence

ORD record
ord-bbe96ca4bb1a410eafb5f52af4ebe059
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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