Cesium carbonate → 7-[(R)-1-(2,6-dichloro-3-fluorophenyl)-ethoxy]-3-phenyl-furo[3,2-c]pyridin-6-ylamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)-ethoxy]-furo[3,2-c]pyridin-6-ylamine (25 mg, 0.0595 mmol), phenylboronic acid (8.7 mg, 0.071 mmol), Cs2CO3 (58 mg, 0.18 mmol), and Pd(PPh3)4 (6.9 mg, 0.006 mmol) in DME (1.5 mL) and H2O (0.5 mL) was degassed and refilled with nitrogen (3×). This mixture was then heated at 100° C. using microwave for 30 min. LC-MS showed completion of the reaction. The reaction mixture was diluted with EtOAc (30 mL), washed with brine (10 mL), and dried over anhydrous sodium sulfate. The residue was purified by silica gel chromatography (Hexane:EtOAc=70:30) to give a brown oil, which was further purified by mass-directed purification to afford the title compound as a brown oil (10.3 mg). 1H NMR (CDCl3, 400 MHz): δ=1.93 (d, J=6.8 Hz, 3H), 6.70 (q, J=6.8 Hz, 1H), 7.10 (dd, J=9.1, 7.8 Hz, 1H), 7.33 (dd, J=9.1, 4.8 Hz, 1H), 7.42-7.55 (m, 5H), 7.67 (s, 1H), 8.12 (s, 1H), 8.18 (s, 1H). MS (ES+): 417.01/418.99 [MH+].

Provenance & Evidence