Dimethylacetamide → HCID 118006339, compound

Participants

Reaction Conditions

Reaction Steps

DMA (1.22 mL) was added to a mixture of (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)bis(1,2-dimethyl-1H-imidazol-5-yl)methanol (70.6 mg, 0.124 mmol, Intermediate 76), zinc cyanide (27.5 mg, 0.234 mmol), Pd2(dba)3 (18.5 mg, 0.0202 mmol), zinc nanopowder (2.5 mg, 0.0382 mmol) and X-Phos (12.9 mg, 0.0262 mmol). The mixture was stirred at 120° C. under argon for 4 hours. After cooling to room temperature, the reaction was diluted with EtOAc (2 mL), filtered through Celite®, and the filter cake washed with EtOAc (2×1 mL). The combined filtrates were washed with 0.75 M aqueous EDTA tetrasodium salt (2×1 mL), water (1×2 mL), and 5 M aqueous NaCl (1×2 mL). The organic layer was diluted with DCM/MeOH, dried (Na2SO4), filtered, and concentrated, and the residue was dry load flash chromatographed with a DCM to 10% MeOH/DCM gradient to provide the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 8.23 (d, J=1.81 Hz, 1H), 7.76 (d, J=9.09 Hz, 1H), 7.55 (d, J=8.59 Hz, 2H), 7.49 (d, J=8.08 Hz, 2H), 7.41 (dd, J=2.06 Hz, 9.04 Hz, 1H), 6.16 (s, 2H), 4.39 (s, 2H), 4.10 (s, 3H), 3.42 (s, 6H), 2.27 (s, 6H); MS m/e 561.3 [M+H]+.

Provenance & Evidence