4-Chlorophenylboronic acid → HCID 11177814, compound

Participants

Reaction Conditions

Reaction Steps

The mixture of 4-amino-3-bromo-7-(3,4,5-trimethoxyphenyl)-thieno[3,2-c]pyridine (30 mg, 0.076 mmol), Pd(PPh3)4 (17 mg, 10 mol %), 4-chlorobenzeneboronic acid (30 mg, 0.19 mmol) and 2M sodium bicarbonate (0.19 ml, 0.38 mmol) in DME (2 ml) was stirred for 14 hours at 80° C. The crude mixture was directly applied to SCX (Varian, 5 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 titled compound (15.5 mg) 1H NMR (400 MHz, DMSO-d6) ppm 7.99 (s, 1H), 7.60 (d, J=8.6 Hz, 2H), 7.58 (s, 1H), 7.51 (d, J=7.3 Hz, 2H), 6.95 ((s, 2H), 5.47 (s, 2H), 3.85 (s, 6H), 3.73 (s, 3H). MS: m/z 427, 429 (M+H)+.

Provenance & Evidence