Potassium Carbonate → Ethyl 8-[(2,6-difluorobenzyl)oxy]-6-ethynyl-2-methylimidazo[1,2-a]pyridine-3-carboxylate

HRID 1844149Notes

Reaction equation

HRID 1844149 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:19]([CH3:21])[N:20]=2)[CH:9]=[C:10]([C:12]#[C:13][Si](C)(C)C)[CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[F:1][C:2]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:19]([CH3:21])[N:20]=2)[CH:9]=[C:10]([C:12]#[CH:13])[CH:11]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86718172Ethyl 8-[(2,6-difluorobenzyl)oxy]-2-methyl-6-[(trimethylsilyl)ethynyl]imidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 86718171Ethyl 8-[(2,6-difluorobenzyl)oxy]-6-ethynyl-2-methylimidazo[1,2-a]pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

720 mg ethyl 8-[(2,6-difluorobenzyl)oxy]-2-methyl-6-[(trimethylsilyl)ethynyl]imidazo[1,2-a]-pyridine-3-carboxylate (Example 37A; 1.63 mmol; 1 equivalent) were initially charged in 16 ml of methanol, and 674 mg of potassium carbonate (4.81 mmol, 3 equivalents) were added. The resulting reaction mixture was stirred at room temperature for 2 h. The reaction mixture was then concentrated, water was added and the mixture was extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution and dried over magnesium sulphate, and the filtrate was concentrated. This gave 587.7 mg of crude product (which contained 35% of the methyl ester of the target compound; quantitative yield) which was used without further purification for the next reaction.

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was then concentrated
  3. additionwater was added
  4. extractionthe mixture was extracted three times with ethyl acetate
  5. washThe combined organic phases were washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. concentrationthe filtrate was concentrated
  8. customquantitative yield) which was used without further purification for the next reaction

Sources & evidence

ORD record
ord-66bdf4b4470e4eea924562e86884ddae
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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