1-Methyl-2-(tributylstannyl)-1H-imidazole → HCID 89793846, compound

Participants

Reaction Steps

A solution of 2-(3-chloro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 425; 34.1 mg, 0.109 mmol), 1-methyl-2-(tributylstannyl)-1H-imidazole (Indofine Chemical Company, Inc.; 0.042 mL, 0.131 mmol) and Pd(PPh3)4 (Strem Chemicals, Inc.; 12.60 mg, 10.90 μmol) in toluene (2.0 mL) was stirred under argon at 110° C. for 1 h. The reaction mixture was then cooled to RT and diluted with hexanes (10 mL). The precipitated solid was collected by vacuum filtration (fine glass frit), sequentially washed with hexanes (10 mL) and Et2O (10 mL), and dried in vacuo to provide 2-(2-methyl-3-(1-methyl-1H-imidazol-2-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (34.7 mg, 0.097 mmol, 89% yield) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.70 (1H, br. s.), 7.97 (1H, dd, J=7.1, 1.3 Hz), 7.91 (1H, s), 7.85 (1H, dd, J=8.2, 1.2 Hz), 7.75-7.82 (1H, m), 7.66 (1H, d, J=0.6 Hz), 7.07 (1H, d, J=2.0 Hz), 6.98 (1H, br. s.), 3.79 (3H, s), 3.42 (2H, td, J=6.8, 2.2 Hz), 2.88 (2H, br. s.), 2.83-2.86 (3H, m). m/z (ESI, +ve) 359.0 (M+H)+.

Provenance & Evidence