M-Cresol → HCID 89783205, compound

Participants

Reaction Steps

Prepared according to Example 103, using NaH as a 60% dispersion in mineral oil (47.0 mg, 1.176 mmol, Sigma Aldrich) in DMF (1679 μl), m-cresol (123 μl, 1.176 mmol, Sigma Aldrich), and 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 50 mg, 0.168 mmol) and heating to 85° C. for 16 h. Purification by reverse phase HPLC (Phenomenex Gemini column, 10 micron, C18, 100 Å, 150×30 mm, 0.1% TFA in ACN/H2O, gradient 5% to 90%) provided 2-(2-(3-methylphenoxy)-8-quinolinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (5.8 mg, 9.4%) as the free base following filtration through a Si-carbonate cartridge (Silicyle) with MeOH. 1H NMR (400 MHz, MeOH-d4) δ ppm 8.37-8.41 (1H, m) 8.10-8.14 (1H, m) 7.73-7.76 (1H, m) 7.46-7.56 (1H, m) 7.28-7.37 (2H, m) 7.14-7.22 (1H, m) 7.04 (3H, s) 3.48-3.55 (2H, m) 3.14-3.19 (2H, m) 2.47 (3H, s). m/z (ESI, +ve) 370.2 (M+H)+.

Provenance & Evidence