m-Toluidine → HCID 89783913, compound

Participants

Reaction Steps

Prepared according to Example 102, using 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 50 mg, 0.168 mmol), 3-methylaniline (91 μl, 0.840 mmol, Sigma Aldrich), and 1.0 M LHMDS in THF (163 μl, 0.840 mmol, Sigma Aldrich) and stirring at 25° C. for 2.h. Purification by column chromatography (silica gel: 0 to 4% MeOH/DCM) provided 2-(2-((3-methylphenyl)amino)-8-quinolinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (2.5 mg, 4%). 1H NMR (400 MHz, MeOH-d4) δ ppm 7.84-7.90 (2H, m) 7.37-7.43 (1H, m) 7.27-7.32 (2H, m) 7.17 (3H, s) 6.88 (2H, m) 3.40 (2H, t, J=1.00 Hz) 2.50 (2H, t, J=1.00 Hz) 2.24 (3H, s). m/z (ESI, +ve) 369.2 (M+H)+.

Provenance & Evidence