Benzenesulfonic Acid → 3-(3-Chloro-4-fluorophenyl)thieno[3,2-c]pyridin-4-amine

Participants

Reaction Conditions

Reaction Steps

The mixture of 4-amino-3-bromo-thieno[3,2-c]pyridine (12) (300 mg 1.24 mmol), 3-chloro-4-fluoro-benzenboronic acid (432 mg, 2.48 mmol), Pd(PPh3)4 (215 mg, 10 mol %) and sodium carbonate (3.1 ml, 6.0 mmol) in 30 ml of DME was stirred for 14 hours at 80° C. The resultant mixture was directly applied to SCX (benzenesulphonicacid-based strong cation exchange sorbent:Varian, 10 g) and eluted with 1N NH3 in CHCl3 and MeOH. The eluant was collected and concentrated in vacuo. The residue was purified by chromatography on a silica gel column to afford the title compound (295 mg). 1H NMR (400 MHz, DMSO-d6) ppm 7.58 (d, J=5.6 Hz, 1H), 7.71 (dd, J=2.1, 7.2 Hz, 1H), 7.57 (s, 1H), 7.54 (dd, J=9.1 Hz, 1H), 7.47 (ddd, J=2.1, 4.8, 8.5 Hz, 1H), 7.29 (d. J=5.8 Hz, 1H), 5.42 (s, 2H). MS: m/z 279, 281 (M+H)+.

Provenance & Evidence