Pyridine → 2-Pyridinecarboxylic acid, 6-fluoro-, 1,1-diMethylethyl ester

HRID 1518414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1518414
S(Cl)(C1C=[CH:9][C:7]([CH3:8])=[CH:6]C=1)(=O)=O.[F:12][C:13]1(C(O)=O)[CH:18]=[CH:17][CH:16]=[CH:15][NH:14]1.N1C=CC=CC=1.[C:28]([O-:31])(O)=[O:29].[Na+]>CC(O)(C)C>[F:12][C:13]1[N:14]=[C:15]([C:28]([O:31][C:7]([CH3:9])([CH3:8])[CH3:6])=[O:29])[CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 67144606HCID 67144606, Verbindung

Produkt 1

HCID 468355932-Pyridinecarboxylic acid, 6-fluoro-, 1,1-diMethylethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

Tosyl chloride (915 mg, 4.8 mmol) was added to a solution of 2-fluoro-picolinic acid (254 mg, 2 mmol) and pyridine (1.08 mL, 13.4 mmol) in 3.6 mL of t-BuOH at 0° C. The reaction was then stirred at room temperature for 12 hours. An aqueous solution of NaHCO3 was then added and the mixture was extracted with ethyl acetate (3 times). The combined organic phases were washed with brine and dried over Na2SO4. The crude compound was purified by flash chromatography using SiO2 (Petroleum Ether/EtOAc 100:0 to 90:10). The product 120A was obtained as a white solid (m=326 mg, 83%): 1HNMR (ppm, CDCl3) 1.6 (s, 9H), 7.05-7.11 (m, 1H), 7.85-7.93 (m, 2H).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate (3 times)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe crude compound was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7c6ce357ad60465dabfeee13c9d72592
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232273B2

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