N-Ethylaniline → 2-(3-(ethyl(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; 24 mg, 0.085 mmol), N-ethylaniline (75 μl, 0.595 mmol, Alfa Aesar, Ward Hill, Mass.), and NaHMDS (1.0M in THF; 595 μl, 0.595 mmol) and heating at 22° C. for 30 min. Purification by silica gel (100% DCM to 4% MeOH/DCM) provided 2-(3-(ethyl(phenyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (40% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.46 (t, J=7.14 Hz, 3H) 2.80 (t, J=6.85 Hz, 2H) 3.61 (td, J=6.90, 2.45 Hz, 2H) 4.10 (q, J=7.24 Hz, 2H) 5.35 (br. s., 1H) 7.14 (d, J=2.15 Hz, 1H) 7.33-7.37 (m, 2H) 7.39-7.45 (m, 2H) 7.51-7.56 (m, 2H) 7.72 (dd, J=8.02, 1.17 Hz, 1H) 7.99 (dd, J=7.63, 1.37 Hz, 1H) 8.35 (s, 1H) 12.12 (br. s., 1H). MS (ESI, pos. ion) m/z: 384.4 (M+1).

Provenance & Evidence