2-Amino-3-methylpyridine → 8-Methyl-2-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridine

HRID 731609Notes

Reaction equation

HRID 731609 reaction equation
Br[CH2:2][C:3]([C:5]1[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:7][O:8][C:9]=1[CH3:10])=O.[NH2:17][C:18]1[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][N:19]=1>C(O)C>[CH3:24][C:23]1[C:18]2[N:19]([CH:2]=[C:3]([C:5]3[C:6]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[N:7][O:8][C:9]=3[CH3:10])[N:17]=2)[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 153472-Amino-3-methylpyridineHCID 27355314-(Bromoacetyl)-5-methyl-3-phenylisoxazole

Product 1

HCID 247381818-Methyl-2-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridineYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(bromoacetyl)-5-methyl-3-phenylisoxazole (commercially available) (112 mg, 0.4 mmol) and 2-amino-3-methylpyridine (43 mg, 0.4 mmol) in ethanol (2.5 mL) was heated under reflux under argon for 5 h. The mixture was then poured onto water and extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulphate and evaporated to leave a yellow oil. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 25:75) afforded the title compound (46 mg, 40%) which was obtained as a colourless oil. MS: m/e=290.3 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under argon for 5 h
  3. additionThe mixture was then poured onto water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were then washed with water and brine
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customto leave a yellow oil
  9. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 25:75)

Sources & evidence

ORD record
ord-b46e1aab8f7e4380982a05125acd88cb
Source dataset
uspto-grants-2009_09
Patent number
US07585874B2

Reaction notes

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