Diisopropylethylamine → 2-(Trifluoromethyl)-4-[(3,3,3-trifluoropropyl)amino]benzonitrile

HRID 2109107

Reaktionsgleichung

F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.Cl.[F:15][C:16]([F:21])([F:20])[CH2:17][CH2:18][NH2:19].CCN(C(C)C)C(C)C>CS(C)=O>[F:11][C:10]([F:13])([F:12])[C:4]1[CH:3]=[C:2]([NH:19][CH2:18][CH2:17][C:16]([F:21])([F:20])[F:15])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Komponenten

Reaktionsbedingungen

Temperatur: 200 °C

Versuchsvorschrift

A mixture of 4-fluoro-2-(trifluoromethyl)benzonitrile (0.158 g, 0.84 mmol), (3,3,3-trifluoropropyl)amine hydrochloride (0.125 g, 0.84 mmol) and DIEA (0.326 g, 2.52 mmol) in 1.5 mL of DMSO was heated in a microwave at 200° C. for 20 min. Upon cooling, the mixture was partitioned between Et2O and 0.1N HCl. The organic phase was washed with 0.1N HCl (×2) and brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (10-80% EtOAc-hexanes gradient) and the product crystallized from Et2O-hexanes to give 0.144 g (61% yield) of the title compound: 1H NMR (400 MHz, CDCl3) δ 7.60 (d, J=8.6 Hz, 1H), 6.87 (d, J=2.4 Hz, 1H), 6.71 (dd, J=8.6, 2.4 Hz, 1H), 4.56 (bs, NH), 3.53 (q, J=6.5 Hz, 2H), 2.51-2.40 (m, 2H).

Aufarbeitung

temperatureUpon cooling
customthe mixture was partitioned between Et2O and 0.1N HCl
washThe organic phase was washed with 0.1N HCl (×2) and brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residue was purified by silica gel chromatography (10-80% EtOAc-hexanes gradient)
customthe product crystallized from Et2O-hexanes

Quellen und Nachweise

ORD-Eintrag: ord-aa12b364963f40a2a4f7b041334ae5a4
Quelldatensatz: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07514470B2

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