N-Methylaniline → 2-(3-(methyl(phenyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Participants

Reaction Conditions

Reaction Steps

Prepared similarly to that described in Example 210 using 2-(3-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 210i; 56 mg, 0.198 mmol), N-methylaniline (150 μl, 1.389 mmol, Alfa Aesar, Ward Hill, Mass.), and NaHMDS (1.0M in THF; 1389 μl, 1.389 mmol) and heating at 0° C. for 1 h. Purification by silica gel (100% DCM to 3% MeOH/DCM) provided 2-(3-(methyl(phenyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (46% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.76 (t, J=6.94 Hz, 2H) 3.33 (s, 3H) 3.42 (td, J=6.80, 2.45 Hz, 2H) 6.97 (br. s., 1H) 7.15 (d, J=2.15 Hz, 1H) 7.41-7.49 (m, 2H) 7.50-7.55 (m, 2H) 7.56-7.62 (m, 2H) 7.70 (dd, J=8.02, 1.17 Hz, 1H) 8.01 (dd, J=7.53, 1.27 Hz, 1H) 8.45 (s, 1H) 11.70 (br. s., 1H). MS (ESI, pos. ion) m/z: 370.2 (M+1).

Provenance & Evidence