Sodium Carbonate → HCID 86596051, compound

Participants

Reaction Steps

A mixture of 6-bromopyridine-3-carboxaldehyde (15.00 g, 0.0806 mol), 3-adamantan-1-yl-4-t-butyldimethylsilanyloxyphenyl boronic acid (37.39 g, 0.09677 mmol) and sodium carbonate (1.719 g, 12.44 mmol) in 750 mL of toluene:EtOH (4:1) and 75 mL of water was degassed with argon for 30 minutes. Tetrakis(triphenyl-phosphine)palladium(0) (2.335 g, 0.00202 mmol, 0.025 eq) was added and the mixture heated at reflux under argon overnight. The solution was cooled to room temperature, diluted with ethyl acetate and washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (eluent: hexane:ethyl acetate, 9:1) to give 24.689 g of 6-[3-(1-adamantyl)-4-t-butyldimethylsilanyloxyphenyl]-pyridin-3-carboxaldehyde (68%). 1H NMR (300 MHz; CDCl3): δ 0.39 (s, 6H), 1.06 (s, 9H), 1.79 (brs, 6H), [2.11 (brs), 2.19 (s), 9 H], 6.91 (d, J=8.4 Hz, 1H), 7.75–7.85 (m, 2H), 8.04 (d, J=2.1 Hz, 1H), 8.16 (dd, J1=8.4, J2=2.1 Hz, 1H), 9.06(d, J=2.1 Hz, 1H), 10.09 (s, 1H).

Provenance & Evidence