2-Bromo-5-(trifluoromethyl)benzenamine → 2-(3-Dimethylamino-1-propynyl)-5-(trifluoromethyl)aniline

HRID 502762

Reaktionsgleichung

Reaktionsgleichung von HRID 502762
Br[C:2]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:3]=1[NH2:4].[CH3:13][N:14]([CH3:18])[CH2:15][C:16]#[CH:17].C(N(C(C)C)CC)(C)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I.C(#N)C>[CH3:13][N:14]([CH3:18])[CH2:15][C:16]#[C:17][C:2]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:3]=1[NH2:4]

Komponenten

7

Edukt 3

HCID 679892-Bromo-5-(trifluoromethyl)benzenamineHCID 81531DiisopropylethylamineHCID 81643N,N-Dimethylpropargylamine

Produkt 1

HCID 684639942-(3-Dimethylamino-1-propynyl)-5-(trifluoromethyl)aniline

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A resealable tube was charged with 2-bromo-5-(trifluoromethyl)aniline (1.00 g, 4.16 mmol), 1-dimethylamino-2-propyne (0.520 g, 6.20 mmol), PdCl2(PPh3)2 (0.15 g, 0.21 mmol), copper iodide (0.80 mg, 0.42 mmol), diisopropylethylamine (1.0 mL) and acetonitrile (3.0 mL). The system was purged with argon, the tube sealed and the mixture stirred at room temperature for 20 h. The reaction mixture was filtered through celite and concentrated. The residue was purified via column chromatography on silica gel (gradient elution with 0-10% methanol-dichloromethane) to afford 2-(3-dimethylamino-1-propynyl)-5-(trifluoromethyl)aniline as a brown oil. MS m/z=243 [M+H]+. Calc'd for C12H13F3N2: 242.

Aufarbeitung

  1. customThe system was purged with argon
  2. customthe tube sealed
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationconcentrated
  5. customThe residue was purified via column chromatography on silica gel (gradient elution with 0-10% methanol-dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-ee99837cdf0c48098abafd0fcb1f1e71
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776869B2

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