Aniline → 2-(2-(phenylamino)quinolin-8-yl)oxazolo[4,5-c]pyridin-4(5H)-one

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Reaction Steps

LHMDS (1.0M in THF; 2015 μl, 2.015 mmol) was added to a solution of 2-(2-chloroquinolin-8-yl)oxazolo[4,5-c]pyridin-4(5H)-one (Example 181; 120 mg, 0.403 mmol) and aniline (184 μl, 2.015 mmol) in dioxane (4031 μl) at RT; and the resulting mixture was stirred at RT for 30 min. The mixture was diluted with EtOAc (150 ml), added to a separatory funnel, and washed with saturated aq. NH4Cl (2×100 ml) before the organic layer was separated, dried over Na2SO4, and concentrated. Purification by silica gel (100% DCM to 5% MeOH/DCM) provided 2-(2-(phenylamino)quinolin-8-yl)oxazolo[4,5-c]pyridin-4(5H)-one (14% yield) as a dark orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.87-6.94 (m, 2H) 7.16 (d, J=9.00 Hz, 1H) 7.27 (t, J=7.82 Hz, 2H) 7.45 (t, J=7.63 Hz, 1H) 7.55 (t, J=6.55 Hz, 1H) 7.98 (d, J=6.85 Hz, 1H) 8.10 (d, J=7.83 Hz, 2H) 8.15-8.20 (m, 2H) 9.69 (s, 1H) 11.87 (br. s., 1H). MS (ESI, pos. ion) m/z: 355.1 (M+1).

Provenance & Evidence