Hydrochloric Acid → (2E)-3-[2-Bromo-4-(trifluoromethyl)phenyl]-N-indol-5-ylprop-2-enamide

HRID 2105593노트

반응식

HRID 2105593 반응식
[Br:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=O.Br[C:16]1[CH:21]=[C:20]([C:22](F)(F)F)[CH:19]=[CH:18][C:17]=1C.[Mn]([O-])(=O)(=O)=O.[CH2:32]([N+:34](CC)(CC)CC)[CH3:33].Cl.[OH:42]S([O-])=O.[Na+].[N:47]1[CH:52]=CC=CC=1>>[Br:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1/[CH:4]=[CH:33]/[C:32]([NH:34][C:16]1[CH:21]=[C:20]2[C:19](=[CH:18][CH:17]=1)[NH:47][CH:52]=[CH:22]2)=[O:42]

참가 물질

7

반응물 6

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 676052-Bromo-4-(trifluoromethyl)benzoic acidHCID 27793762-Bromo-1-methyl-4-(trifluoromethyl)benzeneHCID 11218887Tetraethylammonium permanganateHCID 23665763Sodium Bisulfite

생성물 1

HCID 57807978(2E)-3-[2-Bromo-4-(trifluoromethyl)phenyl]-N-indol-5-ylprop-2-enamide

반응 조건

온도
70 °C

실험 절차

2-Bromo-4-(trifluoromethyl)benzoic acid. To a solution of 2-bromo-1-methyl-4-trifluoromethylbenzene (7.6 g, 32 mmol, ABCR) in pyridine (75 mL) was added tetraethylammonium permanganate (24 g, 96 mmol, prepared according to the procedure of Sala, et al. J. Chem. Soc., Chem. Comm. 1978, 253). The reaction mixture was warmed to 70° C. and stirred at that temperature for 30 h. The reaction mixture was allowed to cool to 25° C. and poured into an ice bath containing cond HCl (150 mL) and NaHSO3 (150 g). The mixture turned to a clear aqueous solution and was extracted with EtOAc (4×200 mL). The combined extracts were washed with satd NaCl (200 mL), dried over Na2SO4, filtered and concentrated in vacuo to provide the title product as a white solid. MS (ESI, neg. ion) m/z: 267 (M−1).

후처리

  1. customprepared
  2. temperatureto cool to 25° C.
  3. additionpoured into an ice bath
  4. extractionwas extracted with EtOAc (4×200 mL)
  5. washThe combined extracts were washed with satd NaCl (200 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f7564fe970824333b25da629148b4991
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07579347B2

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