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

HRID 2105593ノート

反応式

HRID 2105593 の反応式
[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]

参加物

7

反応物 6

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

生成物 1

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

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f7564fe970824333b25da629148b4991
出典データセット
uspto-grants-2009_08
特許番号
US07579347B2

反応ノート

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