Reaktionsgleichung
[Br:1][C:2]1[C:3]([C:13]#[CH:14])=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5].CC(C)([O-])C.[K+]>CN1CCCC1=O.[Cl-].[Na+].O>[Br:1][C:2]1[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=[C:4]2[C:3]=1[CH:13]=[CH:14][NH:5]2Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A solution of 3-bromo-2-ethynyl-5-(trifluoromethyl)aniline (7.54 g, 28.6 mmol) in N-methylpyrollidinone (50 mL) was added dropwise to a 0° C. solution of potassium tert-butoxide (6.41 g, 57.1 mmol) in N-methylpyrollidinone (200 mL). The reaction was stirred at ambient temperature for 4 h. The reaction was poured into brine (500 mL) and extracted with ethyl acetate (4×50 mL). The combined organic layers were washed with brine (100 mL), dried with magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel with a gradient of 10% to 25% ethyl acetate/hexanes to give 7.16 g (95%) as a brown oil. 1H-NMR (CDCl3, 400 MHz) δ 8.54 (bs, 1H), 7.63 (s, 1H), 7.53 (s, 1H), 7.40 (t, J=2.8 Hz, 1H), 6.66 (t, J=2.8 Hz, 1H); LC/MS (HPLC method 4): tR=3.280 min, 264.12(MH)+.
Aufarbeitung
- extractionextracted with ethyl acetate (4×50 mL)
- washThe combined organic layers were washed with brine (100 mL)
- dry with materialdried with magnesium sulfate
- customevaporated
- customThe residue was purified by chromatography on silica gel with a gradient of 10% to 25% ethyl acetate/hexanes
- customto give 7.16 g (95%) as a brown oil
Quellen und Nachweise
- ORD-Eintrag
- ord-8a11afdb083f40389d62929d22bf868a
- Quelldatensatz
- uspto-grants-2011_09
- Patentnummer
- US08026257B2
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