Reaktion #90312

Reaktionsgleichung

3-bromo-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

potassium carbonate

→

title compound

Ausbeute 74.5%

4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)aniline

Ausbeute 74.5%

Lösungsmittel

1,2-dimethoxyethane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was degassed with nitrogen for 10 minutes
2. 2
   TemperaturThe reaction was cooled to room temperature
3. 3
   workup.ADDITIONdiluted with ethyl acetate (100 mL)
4. 4
   FiltrationThe resultant salts were filtered
5. 5
   Sonstigethe filtrated layers were separated
6. 6
   SonstigeThe aqueous layer was separated with ethyl acetate (2×25 mL)
7. 7
   TrocknenThe combined organic layers were dried over anhydrous magnesium sulfate
8. 8
   Einengenconcentrated onto Celite®
9. 9
   SonstigePurification by silica gel chromatography

Vorschrift

To 3-bromo-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole (5.64 g, 18.35 mmol) was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (7.42 g, 33.9 mmol), tetrakis(triphenylphosphine) palladium(0) (3.30 g, 2.86 mmol), and potassium carbonate (7.82 g, 56.6 mmol) in 1,2-dimethoxyethane (75 mL) and water (18 mL). The mixture was degassed with nitrogen for 10 minutes. The reaction mixture was heated at 120° C. for 20 h. The reaction was cooled to room temperature and diluted with ethyl acetate (100 mL). The resultant salts were filtered and the filtrated layers were separated. The aqueous layer was separated with ethyl acetate (2×25 mL). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated onto Celite®. Purification by silica gel chromatography using 0-100% ethyl acetate/hexanes as eluent provided the title compound as a yellow solid (4.16 g, 68%): 1H NMR (400 MHz, CDCl3) δ 8.60 (s, 1H), 8.03-7.97 (m, 2H), 7.88 (d, J=8.4 Hz, 2H), 7.77 (d, J=8.5 Hz, 2H), 6.79-6.74 (m, 2H), 3.88 (s, 2H); 13C NMR (101 MHz, CDCl3) δ 163.94, 148.07, 139.68, 129.67, 129.34, 128.04, 127.07, 127.04, 127.00, 126.96, 125.05, 120.50, 119.35, 114.87; 19F NMR (376 MHz, CDCl3) δ −62.43; ESIMS m/z 305.1 ([M+H]+).

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