Toluene → HCID 44554078, compound

Participants

Reaction Steps

LiHMDS (1.4 mL of 1 M solution in PhMe) was added to methyl isobutyrate(134 mg, 1.3 mmol) at 0° C. The solution was stirred for 10-15 min at it before it was transferred to a flask containing 2-{4-[(4-bromophenyl)-5-[(4-chlorophenyl)thio]-1-methyl-1H-imidazol-2-yl}pyridine (Example 15, 200 mg, 0.44 mmol), Pd(dba)2 (25 mg, 0.044 mmol), and tri-t-butylphosphonium tetrafluoroborate (13 mg, 0.044 mmol) in 1 mL of PhMe. After stirring at rt overnight, it was quenched with aqueous NH4Cl and the product was extracted with EtOAc. The combined extracts were washed with water and brine, dried over MgSO4, filtered, and concentrated. The residue was purified on silica gel column chromatography (5-15% EtOAc in hexanes) to give the title compound. 1H NMR (500 MHz, (CDCl3): 8.67 (d, 1H), 8.38 (d, 1H), 8.06 (d, 2H), 7.84 (t, 1H), 7.39 (d, 2H), 7.32 (t, 1H), 7.24 (d, 2H), 7.05 (d, 2H), 4.13 (s, 3H), 3.65 (s, 3H), 1.61 (s, 6H). LCMS: m/z 478 (M+H)+.

Provenance & Evidence