Triphenylphosphine → 6-(4-Fluoro-benzyl)-3-methoxy-2-(3-trifluoromethyl-phenyl)-pyridine

Participants

Reaction Conditions

Reaction Steps

To the 6-bromomethyl-3-methoxy-2-(3-trifluoromethyl-phenyl)-pyridine synthesized above (0.2 g, 0.58 mmol), 4-fluorophenylboronic acid (0.12 g, 0.87 mmol), PPh3 (0.03 g, 0.12 mmol), K3PO4 (0.37 g, 1.73 mmol) and Pd(OAc)2 (0.013 g, 0.058 mmol) was added DME (4.0 mL), and EtOH—H2O (1:1, 1.0 mL). The reaction was stirred at 80° C. for 20 h. The reaction was cooled to room temperature, concentrated. The residue was purified by silica gel column chromatography using 1:1 dichloromethane-hexanes then dichloromethane to afford 0.056 g (22%) of 6-(4-fluoro-benzyl)-3-methoxy-2-(3-trifluoromethyl-phenyl)-pyridine (P-065) as a clear viscous liquid. 1H NMR (CDCl3, 400 MHz): 8.24 (s, 1H), 8.14 (d, J=8.0 Hz, 1H), 7.6-7.64 (m, 1H), 7.52-7.65 (m, 1H), 7.2-7.34 (m, 4H), 6.96-7.05 (m, 2H), 4.14 (s, 2H), 3.85 (s, 3H); MS (APCI+): 362.1 (M+1), LC-MS: 97.2%.

Provenance & Evidence