Lithium Hydroxide → 4-(2-(4,4-Dimethyl-1,2,3,4-tetrahydro-N-(4-methylphenyl)quinolin-7-yl)ethynyl)-2-fluorobenzoic Acid

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Reaction Steps

To a solution of 0.088 g (0.19 mmol) of ethyl 4-(2-(4,4-dimethyl-1,2,3,4-tetrahydro-N-(4-methylphenyl) quinolin-7-yl)ethynyl)-2-fluorobenzoate (Compound 11) in 3.0 mL of tetrahydrofuran and 0.5 mL of methanol was added 0.5 mL (0.5 mmol) of 1.0M aqueous LiOH. The resulting solution was stirred at room temperature for 72 hours. The mixture was concentrated in vacuo, water was added, and the mixture was extracted with ethyl acetate (2x). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by recrystallization from acetonitrile to give the title compound as a solid (77 mg, 90%). PNMR (300 MHz, d6-acetone) d 1.36 (6 H, s), 1.40 (3 H, t, J=7.1 Hz), 1.86 (2 H, t, J=5.9 Hz), 2.34 (3 H, s), 3.62 (2 H, t, J=5.9 Hz), 6.64 (1 H, d, J=1.6 Hz), 6.86 (1 H, dd, J=8.0, 1.6 Hz), ), 7.17 (2 H, d, J=8.3 Hz), 7.25-7.37 (5 H, m), 7.92 (1 H, t, J=7.8 Hz).

Provenance & Evidence