Water → 7-Bromo-2-chloromethylimidazo[1,2-a]pyridine

HRID 1943996Notes

Reaction equation

HRID 1943996 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([CH2:11]O)[N:10]=[C:4]2[CH:3]=1.S(Cl)([Cl:15])=O.O.C([O-])(O)=O.[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([CH2:11][Cl:15])[N:10]=[C:4]2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 58103977(7-Bromoimidazo[1,2-a]pyridin-2-yl)methanol

Product 1

HCID 441183127-Bromo-2-chloromethylimidazo[1,2-a]pyridineYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 110 mg (0.48 mmol) of (7-bromoimidazo[1,2-a]pyrid-2yl)methanol, prepared according to the protocol described in step 8.2, in 8 mL of anhydrous dichloromethane, stirred at room temperature under an inert atmosphere, is added 0.03 mL (0.53 mmol) of thionyl chloride. The reaction mixture is stirred at room temperature for 4 hours, hydrolysed at 0° C. by successive addition of 3 mL of cold water and 5 mL of saturated aqueous NaHCO3 solution and then extracted with three times 10 mL of dichloromethane. The combined organic phases are dried over sodium sulfate and then concentrated under reduced pressure. 80 mg of the expected product are obtained.

Workup

  1. extractionextracted with three times 10 mL of dichloromethane
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb13e4c6d03f42799af95feaa15bb9a3
Source dataset
uspto-grants-2013_03
Patent number
US08394820B2

Reaction notes

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