Reaction #792193

Reaction equation

K2CO3

4-Bromo-1-phenyl-1H-imidazole

furan-2-ylboronic acid

→

4-(furan-2-yl)-1-phenyl-1H-imidazole

Yield 21.4%

Solvents

toluene-methanol

Conditions

Workup

1. 1
   FiltrationIt was then filtered
2. 2
   Washwashed with toluene-MeOH (5 ml)
3. 3
   Concentrationthe filtrate was concentrated
4. 4
   Otherto yield a crude mixture
5. 5
   Othercolumn purified

Procedure

4-Bromo-1-phenyl-1H-imidazole (200 mg, 0.9 mmol), furan-2-ylboronic acid (342 mg, 3 mmol), PEPPSI-iPr (18 mg, 0.026 mmol), and K2CO3 (640 mg, 4.64 mmol) were then combined in toluene-methanol (1:1) (4 ml). The reaction mixture was heated under microwave at 80° C. for 20 minutes. It was then filtered and washed with toluene-MeOH (5 ml), and the filtrate was concentrated to yield a crude mixture. The crude mixture was then column purified using 15-20% ethyl acetate/hexanes to afford the desired 4-(furan-2-yl)-1-phenyl-1H-imidazole (50 mg, 0.19 mmol, yield 21.4%) as a brown sticky liquid with an HPLC purity of 95.5%. LC-MS [M+H] 211 (C13H10N2O+H expected 211.08). The 1H-NMR spectra was in accordance with the chemical structure.

Source