Dimethylacetamide → HCID 131735022, compound

Participants

Reaction Conditions

Reaction Steps

A pressure tube containing (3-benzyl-4-chloro-2-(trifluoromethyl)quinolin-6-yl)(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methanol•TFA (167 mg, 0.220 mmol, Example 100), Pd2(dba)3 (30 mg, 0.033 mmol), dicyclohexyl(2′,4′,6′-triisopropyl-[1,1′-biphenyl]-2-yl)phosphine (X-Phos, 16 mg, 0.034 mmol), zinc cyanide (15 mg, 0.13 mmol) and zinc nanopowder (3.5 mg, 0.054 mmol) in N,N-dimethylacetamide (1 mL) was sparged with nitrogen for 8 minutes, and then heated at 120° C. for 4 hours. The mixture was allowed to cool to room temperature and filtered through a syringe filter. The filtrate was concentrated in vacuo, EtOAc and saturated NH4Cl aqueous solution 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 provide the title compound. 1H NMR (400 MHz, CD3OD) δ 9.02 (s, 1H), 8.34 (d, J=9.09 Hz, 1H), 8.31 (d, J=1.52 Hz, 1H), 8.01 (dd, J=2.02, 9.09 Hz, 1H), 7.44-7.49 (m, 4H), 7.24-7.30 (m, 2H), 7.18-7.24 (m, 1H), 7.06 (d, J=7.58 Hz, 2H), 7.03 (d, J=2.02 Hz, 1H), 4.64 (s, 2H), 3.71 (s, 3H); MS m/e 533.3 [M+H]+.

Provenance & Evidence