2-Amino-5-methylpyridine → 2-[4-(Ethoxycarbonyl)phenyl]-6-methyl-imidazo[1,2-a]pyridine

HRID 35519

Reaction equation

HRID 35519 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.C(=O)(O)[O-].[Na+].Br[CH2:15][C:16]([C:18]1[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=1)=O>C(O)C>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:15]=[C:16]([C:18]3[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=3)[N:1]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 153482-Amino-5-methylpyridineHCID 516892Sodium BicarbonateHCID 11966043Ethyl 4-(2-bromoacetyl)benzoate

Product 1

HCID 136913272-[4-(Ethoxycarbonyl)phenyl]-6-methyl-imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

67 g (0.62 mole) of 2-amino-5-methylpyridine, 86 g (1.02 mole) of sodium bicarbonate and 143 g (0.527 mole) of ethyl 4-(2-bromoacetyl)benzoate are introduced into 1 l of ethanol. The mixture is brought to reflux for 3 hours and left standing for 19 hours, and the solid formed is recovered by filtration, washed copiously with water and dried. It is recrystallized in a dichloromethane/methanol mixture. M.p. 228°-230° C.

Workup

  1. temperatureto reflux for 3 hours
  2. waitleft
  3. customthe solid formed
  4. filtrationis recovered by filtration
  5. washwashed copiously with water
  6. customdried
  7. customIt is recrystallized in a dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-96d705b1b3cb490481bc6f1bde1cbad9
Source dataset
uspto-grants-1988_08
Patent number
US04767755

Linked notes

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