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

HRID 2086140Notes

Reaction equation

HRID 2086140 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. Ethylchloromethylimidate 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-0bd4c8a9730e4fa4914b020d7a1e327c
Source dataset
uspto-grants-2004_04
Patent number
US06723743B1

Reaction notes

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