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

HRID 916885Notes

Reaction equation

HRID 916885 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).

Workup

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

Sources & evidence

ORD record
ord-854b754c341d448681ff6becf055bc04
Source dataset
uspto-grants-2007_09
Patent number
US07271270B2

Reaction notes

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