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

HRID 1518414Notes

Reaction equation

HRID 1518414 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7c6ce357ad60465dabfeee13c9d72592
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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