Pyridine → HCID 58374067, 화합물

HRID 470579노트

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HRID 470579 반응식
[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]([OH:18])=O)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[F:25]C1N=C(F)N=C(F)N=1>ClCCl>[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]([F:25])=[O:18])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 583740941236188-80-9

생성물 1

HCID 58374067HCID 58374067, 화합물수율 96%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a mixture of 3-phenyl-4-(trifluoromethyl)isoxazole-5-carboxylic acid (3.00 g, 11.7 mmol) and pyridine (1.132 mL, 14.0 mmol) in dichloromethane (100 mL) at room temperature was added 2,4,6-trifluoro-1,3,5-triazine (cyanuric fluoride) (1.18 mL, 14.0 mmol). The reaction mixture was stirred at room temperature overnight, diluted with dichloromethane (300 mL), washed with an ice-cold solution of 0.5N aqueous hydrochloric acid (2×100 mL), and the organic layer was collected. The aqueous layer was back-extracted with dichloromethane (200 mL), and the combined organic layers were dried anhydrous sodium sulfate and concentrated to afford 3-phenyl-4-(trifluoromethyl)isoxazole-5-carbonyl fluoride (2.91 g, 11.2 mmol, 96% yield) as a yellow, viscous oil. The product was found to react readily with methanol and on analysis was characterized as the methyl ester, which had an HPLC ret. time=2.56 min.—Column: CHROMOLITH® SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. LC/MS M+1=272.3 (methyl ester).

후처리

  1. washwashed with an ice-cold solution of 0.5N aqueous hydrochloric acid (2×100 mL)
  2. customthe organic layer was collected
  3. extractionThe aqueous layer was back-extracted with dichloromethane (200 mL)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c258eb86e1c24dca96bbb87b7971fc39
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629282B2

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