Ethyl Acetate → 1-(4-Fluorophenyl)-4-oxo-6-(pyridin-3-yl)-1,4-dihydroquinoline-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

Compound E (15 mg, 0.042 mmol, 1.0 eq), 3-pyridinylboronic acid (11 mg, 0.087 mmol, 2.1 eq), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (3.0 mg, 0.0042 mmol, 0.10 eq) and 1N sodium carbonate (0.21 mL, 0.21 mmol, 5.0 eq) were dissolved in dimethoxyethane (0.6 mL) in a microwave vial and heated at 150° C. for 20 minutes in a microwave reactor. The reaction was portioned between ethyl acetate and water and the layers separated. The aqueous phase was extracted with an additional portion of ethyl acetate and the combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by reverse phase chromatography afforded 10.1 mg (68%) of the title compound as white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.21 (d, J=4.3 Hz, 1H), 8.96 (d, J=1.9 Hz, 1H), 8.62 (m, 2H), 8.60 (s, 1H), 8.17 (dt, J=8.0, 1.7 Hz, 1H), 8.09 (dd, J=8.8, 2.3 Hz, 1H), 7.81-7.78 (m, 2H), 7.66 (d, J=4.3 Hz, 1H), 7.57-7.52 (m, 3H), 7.16 (d, J=8.8 Hz, 1H); ES-MS [M+1]+: 360.2.

Provenance & Evidence