Reacción #792195

Ecuación de reacción

4-chloro-phenylboronic acid

thiophen-2-ylboronic acid

4-bromo-1-(4-chlorophenyl)-1H-imidazole

4-Bromo-1-(4-chlorophenyl)-1H-imidazole

2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl

Cs2CO3

4-bromo-1H-imidazole

→

1-(4-chlorophenyl)-4-(thiophen-2-yl)-1H-imidazole

Rendimiento 10.0%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónIt was then filtered
2. 2
   Lavadowashed with ethyl acetate
3. 3
   Concentraciónthe filtrate was concentrated
4. 4
   Otropurified

Procedimiento

The procedure described above for Formula Ic-iii in Example 16 was followed, starting from 4-chloro-phenylboronic acid and 4-bromo-1H-imidazole, to prepare 4-bromo-1-(4-chlorophenyl)-1H-imidazole. 4-Bromo-1-(4-chlorophenyl)-1H-imidazole (150 mg, 0.583 mmol), thiophen-2-ylboronic acid (149 mg, 1.66 mmol), Pd2(dba)3 (27 mg, 0.029 mmol), 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos) (28 mg, 0.058 mmol) and Cs2CO3 (475 mg. 1.459 mmol) were then combined in dioxane (5 ml). The reaction mixture was heated under microwave at 90° C. for 16 hours. It was then filtered and washed with ethyl acetate, and the filtrate was concentrated. The crude material was column purified using 15-20% ethyl acetate/hexanes to yield the desired 1-(4-chlorophenyl)-4-(thiophen-2-yl)-1H-imidazole (16 mg, 0.061 mmol, yield 10%) as a reddish solid. The HPLC purity of the final product was 99.35%. LC-MS [M+H] 261 (C13H9ClN2S+H expected 261.02). The 1H-NMR spectra was in accordance with the chemical structure

Fuente