Ethanol → HCID 86710090, compound

HRID 1468282Notes

Reaction equation

HRID 1468282 reaction equation
Br[CH2:2][C:3](=O)[CH:4]([CH3:6])[CH3:5].[NH2:8][C:9]1[CH:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:12]=[C:11]([CH3:20])[N:10]=1.[CH2:21](O)C>>[CH3:20][C:11]1[N:10]2[CH:2]=[C:3]([C:4]3([CH3:6])[CH2:21][CH2:5]3)[N:8]=[C:9]2[CH:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:12]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 108990371-Bromo-3-methylbutan-2-oneHCID 67440146HCID 67440146, compound

Product 1

HCID 86710090HCID 86710090, compoundYield 21%

Procedure

1-Bromo-3-methylbutan-2-one (4.43 g, 26.8 mmol) was dissolved in ethanol (10 mL), and the solution was stirred under heat and reflux for 2 days after adding ethyl 2-amino-6-methylpyridine-4-carboxylate (3.00 g, 16.7 mmol). The reaction mixture was allowed to cool to room temperature, and extracted with ethyl acetate after adding a sodium hydrogen carbonate aqueous solution. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (heptane/ethyl acetate=80/20→65/35) to give ethyl 5-methyl-2-(1-methylcyclopropyl)imidazo[1,2-a]pyridine-7-carboxylate (835 mg, yield 21%).

Workup

  1. temperatureunder heat
  2. temperaturereflux for 2 days
  3. extractionextracted with ethyl acetate
  4. additionafter adding a sodium hydrogen carbonate aqueous solution
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was then evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (heptane/ethyl acetate=80/20→65/35)

Sources & evidence

ORD record
ord-690f87aac09c4aa89e9b9268cc7a5e83
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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