Dichloromethane → 2-Cyano-1-(4-fluorobenzyl)-5-methanesulfonylindole

HRID 1432254

Reaktionsgleichung

Reaktionsgleichung von HRID 1432254
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:20]([NH2:22])=O)=[CH:4][CH:3]=1.ClCCl.C(N(CC)CC)C.FC(F)(F)C(O)=O>O>[C:20]([C:8]1[N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:24][CH:23]=2)[C:15]2[C:10]([CH:9]=1)=[CH:11][C:12]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:13][CH:14]=2)#[N:22]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 225043691-(4-Fluorobenzyl)-5-methanesulfonylindole-2-carboxamide

Produkt 1

HCID 225044482-Cyano-1-(4-fluorobenzyl)-5-methanesulfonylindoleAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of 1-(4-fluorobenzyl)-5-methanesulfonylindole-2-carboxamide (100 mg) and dichloromethane (2 ml), triethylamine (0.09 ml) and anhydrous trifluoroacetic acid (0.09 ml) were added at 15 to 30° C. and the mixture was stirred at the same temperature for 2 hours. Water was added therto, and the mixture was extracted with dichloromethane. The organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 68 mg of the desired product as a white crystal.

Aufarbeitung

  1. additionwere added at 15 to 30° C.
  2. extractionwas extracted with dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c50a971cca244b8085257912c33eccd5
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612070B2

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