Diisopropylethylamine → N-(1-(5-Chloro-2,3-dimethoxyphenyl)ethyl)-5-fluoro-2-(methylsulfonyl)benzenamine

HRID 1910577Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1910577
[Cl:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[C:5]([O:11][CH3:12])=[C:6]([CH:8]([NH2:10])[CH3:9])[CH:7]=1.F[C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[S:23]([CH3:26])(=[O:25])=[O:24].C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[C:5]([O:11][CH3:12])=[C:6]([CH:8]([NH:10][C:18]2[CH:19]=[C:20]([F:22])[CH:21]=[CH:16][C:17]=2[S:23]([CH3:26])(=[O:25])=[O:24])[CH3:9])[CH:7]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27583362,4-Difluoro-1-(methylsulfonyl)benzeneHCID 509992651-(5-Chloro-2,3-dimethoxyphenyl)ethylamine

Produkt 1

HCID 44240863N-(1-(5-Chloro-2,3-dimethoxyphenyl)ethyl)-5-fluoro-2-(methylsulfonyl)benzenamineAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 1-(5-chloro-2,3-dimethoxy-phenyl)-ethyl amine (1.27 g, 5.89 mmol), 2,4-difluoro-1-methanesulfonyl-benzene (1.25 g, 6.48 mmol) and N,N-diisopropylethylamine (2.1 mL, 11.78 mmol) in acetonitrile was stirred at 80° C. for 48 h. The solvent was concentrated in vacuo, the residue was taken up in dichloromethane and washed with water, dried, and concentrated under reduced pressure to the crude compound which was purified by silica gel column (20% ethyl acetate in hexanes) to afford [1-(5-chloro-2,3-dimethoxy-phenyl)-ethyl]-(5-fluoro-2-methanesulfonyl-phenyl)-amine (700 mg, 32%): 1H NMR (400 MHz, CDCl3): δ 7.74 (dd, 1 H), 6.82 (m, 2 H), 6.73 (dd, 1 H), 6.42 (dd, 1 H), 6.24 (dd, 1 H), 4.82 (m, 1 H), 3.95 (s 3 H), 3.88 (s,3 H), 3.27 (3, 3 H), 1.58 (s, 3 H).

Aufarbeitung

  1. concentrationThe solvent was concentrated in vacuo
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure to the crude compound which
  5. customwas purified by silica gel column (20% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-33a15412e01042978188ee41ede5bcc4
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604021B2

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