2-Butanone, 3-bromo- → 2,3-Dimethyl-8-(2-ethyl-6-methylbenzyloxy)-imidazo[1,2-a]pyridine-6-carboxamide

HRID 427496Notes

Reaction equation

HRID 427496 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH2:12][C:13]2[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:20][CH3:21])=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.Br[CH:23]([CH3:27])[C:24](=O)[CH3:25].C(=O)(O)[O-].[Na+]>C(#N)C>[CH3:27][C:23]1[N:1]=[C:2]2[C:10]([O:11][CH2:12][C:13]3[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=3[CH2:20][CH3:21])=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]2[C:24]=1[CH3:25]

Participants

5

Reactant 3

HCID 131422-Butanone, 3-bromo-HCID 516892Sodium BicarbonateHCID 183574336-Amino-5-(2-ethyl-6-methylbenzyloxy)nicotinamide

Product 1

HCID 98191772,3-Dimethyl-8-(2-ethyl-6-methylbenzyloxy)-imidazo[1,2-a]pyridine-6-carboxamideYield 35.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-amino-5-(2-ethyl-6-methylbenzyloxy)nicotinamide (0.14 g, 0.49 mmol), 3-bromo-2-butanone (0.075 g, 0.49 mmol) and sodium bicarbonate (0.1 g, 1.2 mmol) was added to acetonitrile (3 ml) and was refluxed for 20 h. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using methylene chloride:methanol (9:1) as eluent. Crystallization from acetonitrile gave 0.058 g (35%) of the title compound.

Workup

  1. temperaturewas refluxed for 20 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel
  4. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-8b60a32ff297408e940b6e3bfa71a9f6
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

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