3-Chloroaniline → 1H,4H,5H,6H,7H-pyrrolo[3,2-c]pyridin-4-one

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Reaction Steps

Prepared according to Example 102, using 3-chloroaniline (220 μl, 2.099 mmol, Sigma Aldrich), 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 125 mg, 0.420 mmol). and 1.0 M LHMDS, 1.0M in THF (2099 μl, 2.099 mmol, Sigma Aldrich) and stirring at 25° C. for 30 min. Purification by column chromatography (silica gel 1 to 5% MeOH/DCM) provided 2424(3-chlorophenyl)amino)-8-quinolinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (27 mg, 16.5%). 1H NMR (400 MHz, CDCl3) δ ppm 12.09-12.31 (1H, m) 8.03 (2H, d, J=1.00 Hz) 7.57-7.60 (1H, m) 7.50-7.55 (1H, m) 7.33-7.41 (4H, m) 7.17-7.22 (1H, m) 7.12-7.15 (1H, m) 6.88-6.93 (1H, m) 5.23-5.28 (1H, m) 3.55-3.62 (2H, m) 2.67-2.73 (2H, m). m/z (ESI, +ve) 389.1 (M+H)+.

Provenance & Evidence