Methanol → HCID 755885, compound

HRID 333747Notes

Reaction equation

HRID 333747 reaction equation
[N:1]1[C:2]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.S(Cl)(Cl)=O.[CH3:19]O>>[N:1]1[C:2]([CH2:10][CH2:11][C:12]([O:14][CH3:19])=[O:13])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 280635813-(Imidazo[1,2-a]pyridin-2-yl)propanoic acid

Product 1

HCID 755885HCID 755885, compound

Conditions

Temperature
60 °C

Procedure

To a solution of 3-imidazo[1,2-a]pyridin-2-ylpropanoic acid (472 mg) in methanol (24.8 mL) was added thionyl chloride (0.215 mL), and the mixture was stirred at 60° C. for 3.5 hr. To the reaction mixture was added, under ice-cooling, saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (402 mg).

Workup

  1. additionTo the reaction mixture was added, under ice-
  2. temperaturecooling
  3. extractionsaturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-935f7dfb4a2c4007a138bd830aed739b
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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