2,6-Difluoroaniline → HCID 89783989, compound

Participants

Reaction Conditions

Reaction Steps

Prepared similarly to Example 82 using 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 51 mg, 0.171 mmol), 2,6-difluoroaniline (26.5 mg, 0.206 mmol, Aldrich), BrettPhos (Strem, Newburyport, Mass.; 5.0 mg, 8.56 μmol), and BrettPhos precat (Strem, Newburyport, Mass.; 7.3 mg, 8.56 μmol), heating at 100° C. for 3 h. Purification by silica gel (100% DCM to 20% MeOH/DCM) provided 2-(2-((2,6-difluorophenyl)amino)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (22% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.47 (t, J=6.75 Hz, 2H) 3.33-3.39 (m, 2H) 6.91-6.95 (m, 2H) 7.14 (d, J=9.00 Hz, 1H) 7.28-7.32 (m, 1H) 7.33 (d, J=4.50 Hz, 1H) 7.35-7.40 (m, 1H) 7.44-7.54 (m, 1H) 7.62 (d, J=6.85 Hz, 1H) 8.01-8.06 (m, 1H) 8.18 (d, J=9.00 Hz, 1H) 9.31 (s, 1H) 11.90 (br. s., 1H). 19F NMR (376 MHz, DMSO-d6) δ ppm −117.35 (2F, s). MS (ESI, pos. ion) m/z: 391.2 (M+1).

Provenance & Evidence