Diisopropylethylamine → 1-(2-(3,5-Dimethoxybenzylamino)-4-fluorophenyl)-2,2,2-trifluoroethanone

HRID 2426001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2426001
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][NH2:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[F:13][C:14]([F:26])([F:25])[C:15]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1F)=[O:16].C(N(C(C)C)CC)(C)C>C(#N)C>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1)[CH2:11][NH:12][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[C:15](=[O:16])[C:14]([F:25])([F:26])[F:13]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 420973(3,5-Dimethoxyphenyl)methanamineHCID 247268371-(2,4-Difluorophenyl)-2,2,2-trifluoroethanone

Produkt 1

HCID 587072721-(2-(3,5-Dimethoxybenzylamino)-4-fluorophenyl)-2,2,2-trifluoroethanoneAusbeute 100,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of (3,5-dimethoxyphenyl)methanamine (0.88 g, 5.20 mmol), 2,2,2-trifluoro-1-(2,4-difluorophenyl)ethanone (1.0 g, 4.80 mmol) and diisopropylethylamine (1.6 mL, 9.6 mmol) in acetonitrile was stirred at 40° C. for 48 h. The solvent was concentrated in vacuo, the residue was taken up in dichloromethane and washed with water and brine, dried, and concentrated under reduced pressure to yield 1.73 g of a yellow oil. The residue was purified by PTLC (20% ethyl acetate in hexanes) to give 527 mg (35%) of the desired aniline: 1H NMR (400 MHz, CDCl3) δ 9.27 (br t, 1H), 7.83 (br s, 1H), 6.47-6.40 (m, 5H), 4.42 (d, 2H), 3.79 (s, 6H).

Aufarbeitung

  1. concentrationThe solvent was concentrated in vacuo
  2. washwashed with water and brine
  3. customdried
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-64fc5c17107a4f758c4f2f1b3ef7bc58
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968538B2

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