Cesium carbonate → HCID 86616678, compound

Participants

Reaction Conditions

Reaction Steps

Compound (283) (1.77 g, 5.43 mmol) was dissolved in HCl (4 N in 1,4-dioxane) (15 mL) and the solution was stirred at RT under N2 for 30 min. The reaction mixture was concentrated to give crude 2-(3-fluorophenyl)-3-methyl-6-(methyloxy)-1-naphthalenol (284) as a gold-yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 2.07 (s, 3H), 3.84 (s, 3H), 6.99-7.44 (m, 6H), 8.04 (d, J=9.3 Hz, 1H), 8.75 (s, 1H). Compound 284 (˜1.50 g, 5.32 mmol) was immediately treated with 4-fluoro-2-trifluoromethylbenzaldehyde (1.53 g, 7.96 mmol) and Cs2CO3 (2.59 g, 7.98 mmol) in DMF (5 mL). The mixture was heated at 110° C. for 16 h, cooled to RT and diluted with 100 mL each H2O and EtOAc. The organic layer was washed with 100 mL each water and brine, dried (Na2SO4) and concentrated to 2.92 g of an amber oil. The oil was purified by column chromatography with 10% EtOAc/hexanes to yield 1.57 g (65%) of the title compound 285 as a white foam. 1H NMR (400 MHz, DMSO-d6): δ 2.20 (s, 3H), 3.88 (s, 3H), 6.96 (dd, J1=2.3 Hz, J2=8.6 Hz, 1H), 7.01-7.14 (m, 4H), 7.17 (d, J=2.5 Hz, 1H), 7.23-7.38 (m, 1H), 7.39 (d, J=2.5 Hz, 1H), 7.93 (d, J=9.1 Hz, 1H), 7.79 (s, 1H), 7.90 (d, J=8.7 Hz, 1H), 10.02 (s, 1H).

Provenance & Evidence