Chloroform → 2-(Chloromethyl)-3-propyl-3H-imidazo[4,5-b]pyridine

HRID 1816420Notes

Reaction equation

HRID 1816420 reaction equation
NC(C)C[C:4]1[C:9]([NH2:10])=[CH:8][CH:7]=[CH:6][N:5]=1.C([O-])([O-])=O.[K+].[K+].[CH:18]([Cl:21])(Cl)Cl>>[CH2:4]([N:5]1[C:4]2[N:5]=[CH:6][CH:7]=[CH:8][C:9]=2[N:10]=[C:6]1[CH2:18][Cl:21])[CH2:9][CH3:8]

Participants

4

Reactant 3

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 22493781HCID 22493781, compound

Product 1

HCID 224938472-(Chloromethyl)-3-propyl-3H-imidazo[4,5-b]pyridine

Procedure

2-aminopropyl-3-aminopyridine (172) (5.3 g, 35 mmol) is dissolved in 100 mL CHCl3 at room temperature. Ethyl chloromethylimidate hydrochloride (14 g, 89 mmol) is added followed by K2CO3 (25 g, 180 mmol). The suspension was stirred vigorously at room temperature for 3 hours. The reaction mixture is filtered through Celite and the solvent removed in vacuo. The residue is passed through a short plug of silica gel eluting with ethyl acetate to afford 3.7 g of 1-propyl-2-chloromethyl-7-azabenzimidazole (183). 1-propyl-2-(4-methoxybenzylamino)methyl-7-azabenzimidazole.

Workup

  1. filtrationThe reaction mixture is filtered through Celite
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-57e5eb4af3794c38ab2a662dddfa215e
Source dataset
uspto-grants-2005_04
Patent number
US06884815B1

Reaction notes

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