Tetrafluoro-m-phenylenediamine dihydrochloride → 2-Chloro-4-(8-{4-[(dimethylamino)methyl]phenylamino}-7-(methylsulfonyl)-1,5-naphthyridin-2-yl)-6-fluorophenol 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-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (58 mg, 0.21 mmol) followed by formation of the dihydrochloride salt to afford the desired product (51 mg, 63%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.12 (s, 1H), 8.46 (d, J=9.0 Hz, 1H), 8.37 (d, J=9.1 Hz, 1H), 7.68-7.61 (m, 2H), 7.60-7.53 (m, 2H), 7.22 (t, J=1.8 Hz, 1H), 7.06 (dd, J=11.9, 2.2 Hz, 1H), 4.43 (s, 2H), 3.48 (s, 3H), 2.88 (s, 6H); ESI MS m/z 501 [M+H]+; HPLC>99% (AUC), tR=10.68 min.

Provenance & Evidence