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

HRID 1518414노트

반응식

HRID 1518414 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7c6ce357ad60465dabfeee13c9d72592
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232273B2

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