Lithium Hexamethyldisilazide → HCID 44553733, compound

Participants

Reaction Conditions

Reaction Steps

2-{4-(4-Bromophenyl)-5-[(4-chlorophenyl)thio]-1-methyl-1H-imidazol-2-yl}pyridine (Example 15, 300 mg, 0.57 mmol), Pd(dba)2 (19 mg, 0.03 mmol), and biphenyl-PCy2 (11.5 mg, 0.03 mmol) were charged into a flask that was flushed with nitrogen. Toluene (2.2 mL) was added, followed by LiHMDS (1M in PhMe, 2 mL, 2 mmol). After heating at 75° C. overnight, the reaction was quenched with aqueous NH4Cl and diluted with EtOAc. The organic layer was washed with water and brine. The volatiles were evaporated and the residue was purified by reverse phase HPLC to afford the title compound. 1H NMR (500 MHz, (CD3OD): 8.58 (broads, 1H), 8.18 (broad s, 1H), 7.98 (t, 1H), 8.27 (d, 2H), 7.68 (d, 2H), 7.46 (broad s, 7.07 (d, 2H), 6.78 (d, 2H), 3.98 (s, 3H). LCMS: m/z 393 (M+H)+.

Provenance & Evidence