Tetrafluoro-m-phenylenediamine dihydrochloride → 2,6-Dichloro-4-(8-{4-[(dimethylamino)methyl]phenylamino}-7-(methylsulfonyl)-1,5-naphthyridin-2-yl)phenol dihydrochloride

Participants

Reaction Steps

Following general procedure II, 6-chloro-N-{4-[(dimethylamino)methyl]phenyl}-3-(methylsulfonyl)-1,5-naphthyridin-4-amine (50 mg, 0.14 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (61 mg, 0.21 mmol) followed by formation of the dihydrochloride salt to afford the desired product (35 mg, 42%) as an orange solid: 1H NMR (500 MHz, CD3OD) δ 9.12 (s, 1H), 8.47 (d, J=9.1 Hz, 1H), 8.38 (d, J=9.2 Hz, 1H), 7.63 (d, J=9.0 Hz, 2H), 7.59-7.52 (m, 2H), 7.34 (s, 2H), 4.43 (s, 2H), 3.48 (s, 3H), 2.86 (s, 6H); ESI MS m/z 517 [M+H]+; HPLC>99% (AUC), tR=11.03 min.

Provenance & Evidence