Ethanol → HCID 71108835, compound

HRID 64410Notes

Reaction equation

HRID 64410 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([CH:15]=[C:16]([CH3:18])[N:17]=2)[CH:9]=[C:10]([C:12]([OH:14])=[O:13])[CH:11]=1.S(=O)(=O)(O)O.[CH2:28](O)[CH3:29]>>[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([CH:15]=[C:16]([CH3:18])[N:17]=2)[CH:9]=[C:10]([C:12]([O:14][CH2:28][CH3:29])=[O:13])[CH:11]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 86713418HCID 86713418, compound

Product 1

HCID 71108835HCID 71108835, compound

Procedure

To 350 mg of 8-[(2-fluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-6-carboxylic acid were added 18 ml of ethanol and 200 μl of sulfuric acid, followed by heating to reflux overnight. Under reduced pressure, the solvent was removed by filtration to around one third of the amount thereof, and a saturated aqueous sodium hydrogen carbonate solution and chloroform were then added thereto to carry out a layer separation operation. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 330 mg of ethyl 8-[(2-fluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-6-carboxylate.

Workup

  1. temperatureby heating
  2. temperatureto reflux overnight
  3. customUnder reduced pressure, the solvent was removed by filtration to around one third of the amount
  4. additiona saturated aqueous sodium hydrogen carbonate solution and chloroform were then added
  5. customa layer separation operation
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9ff50a679ea74633aba031d749ee44b5
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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