Propanal → N-[8-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N,N-dipropylamine

HRID 501000Notes

Reaction equation

HRID 501000 reaction equation
[Br:1][C:2]1[C:3]2[N:4]([C:9]([NH:14][CH2:15][CH2:16][CH3:17])=[C:10]([S:12][CH3:13])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH:18](=O)[CH2:19][CH3:20].S(=O)(=O)(O)O.[BH4-].[Na+].[OH-].[Na+]>O1CCCC1.O>[Br:1][C:2]1[C:3]2[N:4]([C:9]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[C:10]([S:12][CH3:13])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

8

Reactant 5

HCID 527PropanalHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 22024391N-[8-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N-propylamine

Product 1

HCID 22024469N-[8-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N,N-dipropylamineYield 67.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-[8-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N-propylamine (103 mg) and propionaldehyde (57 mg) were dissolved in tetrahydrofuran (1:2 mL), then 3M sulfuric acid (0.24 mL) was added thereto, followed by adding sodium borohydride (24 mg) under ice-cooling, and then the mixture was stirred for 3 hours. Water was added to the reaction mixture, which was neutralized with a 2N aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:9) to give the title compound (79 mg) as a white powder.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:9)

Sources & evidence

ORD record
ord-043754c2519848a5876d623224d4845a
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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