Dimethylacetamide → HCID 86716142, compound

Participants

Reaction Conditions

Reaction Steps

A pressure tube containing (4-chloro-3-phenyl-2-(trifluoromethyl)quinolin-6-yl)(1-methyl-1H-imidazol-5-yl)(6-(trifluoromethyl)pyridin-3-yl)methanol•TFA (101 mg, 0.128 mmol, Example 172), Pd2 dba3 (12 mg, 0.013 mmol), dicyclohexyl(2′,4′,6′-triisopropyl-[1,1′-biphenyl]-2-yl)phosphine (X-Phos, 6.3 mg, 0.013 mmol), zinc cyanide (10 mg, 0.085 mmol), and zinc nanopowder (2.5 mg, 0.038 mmol) in N,N-dimethylacetamide (1 mL) was purged with nitrogen for 5 min, and then heated at 120° C. for 2.5 hours. The mixture was allowed to cool to room temperature and filtered through a syringe filter. The filtrate was concentrated in vacuo, and EtOAc and NH4OH (aqueous) were added. The organic layer was separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was purified by reverse phase HPLC (water/acetonitrile/0.1% TFA) to give the title compound as a white solid. 1H NMR (400 MHz, MeOD-d4) δ 9.06 (s, 1H), 8.87 (d, J=2.02 Hz, 1H), 8.38-8.47 (m, 2H), 8.14 (dd, J=2.27, 8.34 Hz, 1H), 8.05 (dd, J=2.02, 9.09 Hz, 1H), 7.91 (d, J=8.08 Hz, 1H), 7.52-7.62 (m, 3H), 7.47 (d, J=6.06 Hz, 2H), 7.19 (s, 1H), 3.72 (s, 3H); MS m/e 554.1 [M+H]

Provenance & Evidence