Ammonium Chloride → N-3-isoxazolyl-1-(2-methoxy-5-(2-pyridinyl)phenyl)-2-oxo-1,2-dihydro-6-quinolinesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a vial charged with 1-(5-bromo-2-methoxyphenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.100 g, 0.210 mmol) and Pd(Ph3P)4 (0.024 g, 0.021 mmol) in THF (1.050 ml) was added pyridin-2-ylzinc(II) bromide (0.5M in THF) (2.100 ml, 1.050 mmol). The reaction was sealed and heated to 60° C. for 6.5 h. After cooling to RT, ammonium chloride (sat. aq) was added and the product extracted (×3) with DCM. The organics were dried via phase separator and concentrated in vacuo. The crude material was purified via MPLC, eluting with 20-100% ethyl acetate in heptanes to yield desired product, contaminated with triphenylphosphine oxide. The material was triturated in diethyl ether and filtered to yield N-(isoxazol-3-yl)-1-(2-methoxy-5-(pyridin-2-yl)phenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.070 g, 0.148 mmol, 70.3% yield) as a light yellow solid. MS (ESL pos. ion) m/z: [M+1] 475.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.74 (s, 3 H) 6.44 (d, J=1.76 Hz, 1 H) 6.79-6.85 (m, 2 H) 7.31 (t, J=5.85 Hz, 1 H) 7.42 (d, J=8.81 Hz, 1H) 7.52-7.67 (m, 2 H) 7.97 (d, J=8.01 Hz, 1 H) 8.06 (d, J=2.28 Hz, 1 H) 8.23 (d, J=9.64 Hz, 1 H) 8.31-8.41 (m, 2 H) 8.59-8.64 (m, 1 H) 8.72 (d, J=1.87 Hz, 1 H) 11.59-11.69 (m, 1 H).

Provenance & Evidence