4-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamine → N-[4-[(6,7-dimethoxy-4-quinolyl)oxy]-3-fluoro-phenyl]-4-ethoxy-1-(4-fluorophenyl)pyrazole-3-carboxamide

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Reaction Steps

Acid chloride D4 (0.17 mmol, 1.0 eq.) was dissolved in dry pyridine (1.5 mL) at 0° C. and A2 (34 mg, 0.11 mmol, 0.65 eq.) was added. The reaction was allowed to reach RT overnight. The mixture was diluted with EtOAc and washed twice with aq. KOH-solution (0.5N), twice with aq. sat. NH4Cl-solution, and finally once with brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (DCM/MeOH=100:0 to 10:1) to yield the desired product D5 (31 mg, 52% over 2 steps) as a white solid. 1H NMR (400 MHz, d6-DMSO, 300K) δ 1.38 (t, J=7.0 Hz, 3H), 3.94 (s, 6H), 4.09 (q, J=7.0 Hz, 2H), 6.48 (d, J=5.3 Hz, 1H), 7.43 (m, 4H), 7.53 (s, 1H), 7.70 (d, J=9.4 Hz, 1H), 8.01 (m, 3H), 8.47 (m, 2H), 10.17 (s, 1H). MS (ES) C29H24F2N4O5 requires: 546. Found: 547 (M+H)+.

Provenance & Evidence