Toluene → Methyl 2-(4-diethylaminophenyl)-2-phenyl-6-(4'-pentylbiphenyl-4-yl)-2H-naphtho[1,2-b]pyran-5-carboxylate

Participants

Reaction Steps

A solution containing methyl 2-(4-diethylamino-phenyl)-2-phenyl-6-trifluoromethanesulfonyloxy-2H-naphtho[1,2-b]pyran-5-carboxylate (0.90 g, 1.47 mmol), 4′-pentyl-4-biphenylboronic acid (0.39 g. 1.47 mmol), K2CO3 (0.30 g), PhMe (30 mL), ethanol (30 mL) and degassed for 1 h. Pd(PPh3)4 (0.085 g, 5% mol) was added and the reaction mixture was heated at reflux for 16 hrs. The reaction mixture was poured into water (100 mL), extracted with DCM (4×50 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was chromatographed on silica using DCM (20% hexanes) and recrystallised from acetone-MeOH to give a pale blue powder (2.3 g, 30%) mp: 177-178° C.

Provenance & Evidence