3-Pyridinemethanol → Methyl 1-(4-fluorophenyl)-4-oxo-6-(pyridin-3-ylmethoxy)-1,4-dihydroquinoline-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

Compound L (15 mg, 0.048 mmol, 1.0 eq) and 3-pyridinemethanol (10 mg, 0.096 mmol, 2.0 eq) were dissolved in THF (0.5 mL) and cooled to 0° C. Triphenylphosphine (28 mg, 0.11 mmol, 2.2 eq) and di-tert-butylazodicarboxylate (18 mg, 0.077 mmol, 1.6 eq) were added and the reaction was stirred at room temperature until complete by LCMS. The reaction was concentrated and purified using reverse phase chromatography to afford 15 mg (77%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.69 (d, J=1.7 Hz, 1H), 8.54 (dd, J=4.7, 1.3 Hz, 1H), 8.41 (s, 1H), 7.90-7.88 (m, 1H), 7.79 (d, J=3.0 Hz, 1H), 7.73-7.70 (m, 2H), 7.50 (t, J=8.8 Hz, 2H), 7.43 (dd, J=7.8, 4.8 Hz, 1H), 7.37 (dd, J=9.3, 3.0 Hz, 1H) 6.94 (d, J=9.2 Hz, 1H), 5.28 (s, 2H), 3.72 (s, 3H); ES-MS [M+1]+: 405.2.

Provenance & Evidence