Pyridine → 5-(Pyridin-2-yl)-4-(trifluoromethyl)isoxazole-3-carbonyl fluoride

HRID 1951937노트

반응식

HRID 1951937 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[O:11][N:10]=[C:9]([C:12](O)=[O:13])[C:8]=1[C:15]([F:18])([F:17])[F:16].N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:27]>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[O:11][N:10]=[C:9]([C:12]([F:27])=[O:13])[C:8]=1[C:15]([F:18])([F:17])[F:16]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 580628175-(Pyridin-2-yl)-4-(trifluoromethyl)isoxazole-3-carboxylic acid

생성물 1

HCID 580628345-(Pyridin-2-yl)-4-(trifluoromethyl)isoxazole-3-carbonyl fluoride수율 88.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 5-(pyridin-2-yl)-4-(trifluoromethyl)isoxazole-3-carboxylic acid (54.3 mg, 0.210 mmol) and pyridine (0.037 mL, 0.463 mmol) in dichloromethane (2 mL) was added cyanuric fluoride (0.021 mL, 0.252 mmol). The reaction mixture was stirred at room temperature for 2 hrs., diluted with dichloromethane (2 mL), and washed with ice water (1 mL). The aqueous layer was extracted with dichloromethane (2×1 mL), and the combined organic layers were washed with brine (1 mL) and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded 5-(pyridin-2-yl)-4-(trifluoromethyl)isoxazole-3-carbonyl fluoride (0.048 g, 0.185 mmol, 88% yield). The product had an HPLC retention. time=2.50 min. (The product reacted readily with methanol and a small portion was characterized as the methyl ester)—Column: YMC S5 COMBISCREEN® 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA.

후처리

  1. washwashed with ice water (1 mL)
  2. extractionThe aqueous layer was extracted with dichloromethane (2×1 mL)
  3. washthe combined organic layers were washed with brine (1 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationConcentration under reduced pressure

출처 및 근거

ORD 기록
ord-f9780144861d44efb19b8775afd9a67e
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404672B2

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