4-Aminopyridine → HCID 89783665, compound

Participants

Reaction Conditions

Reaction Steps

Prepared similarly to that described in Example 82 using 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 58 mg, 0.195 mmol), pyridin-4-amine (22.00 mg, 0.234 mmol, Aldrich), BrettPhos precat (Strem, Newburyport, Mass.; 8.25 mg, 9.74 μmmol), Brettphos (Strem, Newburyport, Mass.; 5.70 mg, 9.74 μmmol), and LHMDS (1.0M in THF; 429 μl, 0.429 mmol), heating at 150° C. for 40 min in a microwave (Biotage Initiator). Purification by silica gel chromatography (100% DCM to 10% MeOH/DCM) provided 2-(2-(pyridin-4-ylamino)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (13% yield). 1H NMR (400 MHz, MeOH-d4) δ ppm 2.85 (t, J=7.04 Hz, 2H) 3.62 (t, J=7.04 Hz, 2H) 6.99 (s, 1H) 7.11 (d, J=9.00 Hz, 1H) 7.39 (t, J=7.73 Hz, 1H) 7.64 (dd, J=8.02, 1.17 Hz, 1H) 7.75 (d, J=6.46 Hz, 2H) 7.94 (dd, J=7.43, 1.17 Hz, 1H) 8.14 (d, J=8.80 Hz, 1H) 8.33 (d, J=6.26 Hz, 2H). MS (ESI, pos. ion) m/z: 356.3 (M+1).

Provenance & Evidence