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

HRID 1518414ノート

反応式

HRID 1518414 の反応式
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

参加物

6

反応物 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 67144606HCID 67144606、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7c6ce357ad60465dabfeee13c9d72592
出典データセット
uspto-grants-2012_07
特許番号
US08232273B2

反応ノート

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