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

HRID 1951937ノート

反応式

HRID 1951937 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f9780144861d44efb19b8775afd9a67e
出典データセット
uspto-grants-2013_03
特許番号
US08404672B2

反応ノート

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