Pyridine → 3-amino-4-bromo-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide

HRID 1943094노트

반응식

HRID 1943094 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4](Cl)[C:3]=1N.N1C=CC=C[CH:21]=1.S(=[N:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][C:37]=1[Br:38])[C:32](Cl)=[O:33])=O.C[N:40]([CH3:43])C=O>ClCCl>[NH2:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][C:37]=1[Br:38])[C:32]([NH:40][C:43]1[C:4]([CH3:3])=[CH:5][C:6]([C:8]([F:17])([C:13]([F:15])([F:14])[F:16])[C:9]([F:10])([F:12])[F:11])=[CH:7][C:2]=1[CH3:21])=[O:33]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 100194962,6-Dichloro-4-(perfluoropropan-2-yl)anilineHCID 594448243-Sulfinylamino-4-bromo-benzoyl chloride

생성물 1

HCID 594448253-amino-4-bromo-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2,6-dichloro-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenylamine (1.02 g, 3.1 mmol) (Example 6.3) in anhydrous dichloromethane (25 ml), at 20° C., was added sequentially pyridine (0.74 g, 2.0 mmol) and 4-bromo-3-sulfinylamino-benzoyl chloride (0.94 g, 9.30 mmol) (Example 1.2). The reaction mixture was stirred at ambient temperature for one hour. The reaction mixture was then heated to 50° C. for 16 hours. The reaction mixture was allowed to cool to ambient temperature before adding dimethylformamide (50 ml). The dichloromethane was distilled off and the reaction mixture was heated to 130° C. for 16 hours. The reaction was quenched by addition of aqueous sodium hydrogen carbonate (saturated) (10 ml). After separation of the phases, the aqueous layer was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:5 to 1:0) to give 3-amino-4-bromo-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide (quantitative, 100% yield). 1H-NMR (CDCl3, 400 MHz): 7.73 (m, 3H), 7.27 (m, 3H), 6.91 (m, 1H), 3.9 (s, 2H) ppm.

후처리

  1. temperatureThe reaction mixture was then heated to 50° C. for 16 hours
  2. temperatureto cool to ambient temperature
  3. distillationThe dichloromethane was distilled off
  4. temperaturethe reaction mixture was heated to 130° C. for 16 hours
  5. customThe reaction was quenched by addition of aqueous sodium hydrogen carbonate (saturated) (10 ml)
  6. customAfter separation of the phases
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. dry with materialThe combined organic phases were dried over sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:5 to 1:0)

출처 및 근거

ORD 기록
ord-247be295ece74cfa8b50c64459aefb13
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389767B2

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