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

HRID 1624091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1624091
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a9006c7723774d7aa82e646f2a9c3800
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778964B2

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