Thionyl Chloride → 2-Chloromethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine

HRID 586372Notes

Reaction equation

HRID 586372 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[N:8]=[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]2[C:15]=1[CH2:16][CH2:17][CH3:18]>C(Cl)Cl.CCOC(C)=O>[Cl:3][CH2:6][C:7]1[N:8]=[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]2[C:15]=1[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 223350472-Hydroxymethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine

Product 1

HCID 223350602-Chloromethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Thionyl chloride (125 mg, 1.06 mmol) is added to a solution of 2-hydroxymethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine (100 mg, 0.53 mmol) in CH2Cl2 (3 mL) at 0° C. under nitrogen with magnetic stirring. After 1 hour, the reaction is diluted with EtOAc (20 mL), washed with saturated aqueous NaHCO3 (10 mL), water (10 mL) and brine (10 mL). The solution is then dried over anhydrous sodium sulfate, filtered and evaporated at reduced pressure to obtain 2-chloromethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine as a colorless oil. TLC (10% MeOH/CH2Cl2) Rf=0.60. Step 5. Preparation of 3-{1-[(3-propylimidazo[1,2-a]pyridin-2-yl)methyl]-1H-imidazol-2-yl}benzonitrile

Workup

  1. washwashed with saturated aqueous NaHCO3 (10 mL), water (10 mL) and brine (10 mL)
  2. dry with materialThe solution is then dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-8ad0518c2cf24898b0c7b4a219712732
Source dataset
uspto-grants-2005_08
Patent number
US06936617B2

Reaction notes

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