Chloroacetone → 5-Bromo-2-methylimidazo[1,2-a]pyridine

HRID 1922748Notes

Reaction equation

HRID 1922748 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.Cl[CH2:10][C:11](=O)[CH3:12]>>[Br:1][C:2]1[N:7]2[CH:10]=[C:11]([CH3:12])[N:8]=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6571ChloroacetoneHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 126377285-Bromo-2-methylimidazo[1,2-a]pyridineYield 45%

Procedure

A mixture of 6-bromopyridin-2-ylamine (1.0 g, 5 6 mmol) and 1-chloropropan-2-one (0.5 mL, 6.3 mmol) in IMS (4 mL) was stirred at reflux for 36 hours, then cooled to room temperature and loaded onto an Isolute® SCX-2 cartridge (20 g). The cartridge was washed with MeOH then the desired product eluted with 2 M NH3 in MeOH. After the solvents were removed, the residue was purified by flash chromatography (Si—PPC, MeOH:Et2O, gradient 0:100 to 10:100) to give 5-Bromo-2-methylimidazo[1,2-a]pyridine as a yellow oil (547 mg, 45%). LCMS (Method H): RT=0.31 min and 2.04 min, [M+H]+ 211(79Br) and 213(81Br)

Workup

  1. temperatureat reflux for 36 hours
  2. washThe cartridge was washed with MeOH
  3. washthe desired product eluted with 2 M NH3 in MeOH
  4. customAfter the solvents were removed
  5. customthe residue was purified by flash chromatography (Si—PPC, MeOH:Et2O, gradient 0:100 to 10:100)

Sources & evidence

ORD record
ord-549bd27b1cae452ba243e1c21f6b9125
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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