4-Fluorophenylboronic acid → 2-Cyclopropyl-1-(4-fluoro-phenyl)-4-iodo-1H-imidazole
Reaction equation
[CH:1]1([C:4]2[NH:5][CH:6]=[C:7]([I:9])[N:8]=2)[CH2:3][CH2:2]1.[F:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1>C1COCC1>[CH:1]1([C:4]2[N:5]([C:14]3[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=3)[CH:6]=[C:7]([I:9])[N:8]=2)[CH2:3][CH2:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Cyclopropyl-4-iodo-1H-imidazole (500 mg, 2.14 mmol) was dissolved in 20 ml THF. 4-Fluorobenzene boronic acid (613 mg, 4.38 mmol) and [Cu(OH)TMEDA]2Cl2 (347 mg, 0.75 mmol) were added. Oxygen was bubbled through the reaction mixture for 60 min and stirring was continued under an oxygen atmosphere at RT overnight. The reaction mixture was filtered through a dicalite speed plus pad and washed with 30 mL ethyl acetate. After drying the crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 90:10→50:50 gradient) to get the desired compound as a white solid (320 mg, 46%), MS: m/e=329.1 (M+H+). Preparation of the Compounds of Formula I