Potassium Carbonate → [3,5-Bis(trifluoromethyl)benzyl](2-bromo-5-nitrobenzyl)amine

HRID 17039

Reaktionsgleichung

CS(O[CH2:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[Br:16])(=O)=O.[F:17][C:18]([F:32])([F:31])[C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[CH2:22][NH2:23].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O.CCCCCC>CN(C=O)C.O>[F:17][C:18]([F:31])([F:32])[C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:26]=1)[CH2:22][NH:23][CH2:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[Br:16]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of 2-bromo-5-nitrobenzyl methanesulfonate from Step B (0.42 g, 1.35 mmol) and 3,5-bis-trifluoromethyl benzylamine (0.33 g, 1.35 mmol) in DMF (10 ml) at 0° C., potassium carbonate (0.37 g, 2.69 mmol) was added. The mixture was stirred at 0° C. for 2 h. TLC analysis (EtOAc/hexane=2:8) showed completion of the reaction. Water (50 ml) was added. The mixture was extracted with EtOAc (3×40 ml). The combined organic layers were washed with brine, and dried over sodium sulfate. The title compound was obtained by flash column chromatography using 2:8 EtOAc/hexane as the eluant. 1H NMR (CDCl3, 500 MHz) δ 8.35 (d, J=2.5 Hz, 1H), 8.03 (dd, J=8.5, 2.5 Hz, 1H), 7.88 (s, 2H), 7.81 (s, 1H), 8.76 (d, J=8.5 Hz, 1H), 4.00 (s, 4H).

Aufarbeitung

customcompletion of the reaction
extractionThe mixture was extracted with EtOAc (3×40 ml)
washThe combined organic layers were washed with brine
dry with materialdried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag: ord-01c64f527dae46e1bfa7b838e4d4470f
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07737295B2

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