Sodium Carbonate → HCID 57808558, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-Chloro-2-(4-methylphenyl)-3-phenylpyridine (10-2; 0.050 g, 0.179 mmol), bis(pinacoloto)diboron (0.054 g, 0.214 mmol), potassium acetate (0.026 g, 0.268 mmol), Pd2(dba)3 (5 mg, 0.005 mmol) tricyclohexylphosphine (4 mg, 0.013 mmol) in anhydrous dioxane (2 mL) was degassed (3× pump/N2) and heated at 160° C. in the microwave for 1 hr. forms the boronic acid. In the same pot, 2-bromopyrimidine (0.042 g, 0.26mmol), tetrakis(triphenylphosphine)palladium (0.010 g, 0.00895 mmol), and 2M aq Na2CO3 (1 mL) were added and the resulting mixture was degassed (3× pump/N2) and heated in the microwave at 150° C. for 3 hr. Reaction partitioned between CH2Cl2 and water, extracted 3× with CH2Cl2, and the combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography (10-20% EtOAc in Hexanes) to give the title compound. 1H-NMR (500 MHz, CDCl3) δ 9.69 (d, 1H, J=2.0 Hz), 8.86 (d, 2H, J=4.9 Hz), 8.73 (d, 1H, J=2.0 Hz), 7.37-7.23 (m, 8H), 7.08 (d, 2H J=7.82 Hz), 2.33 (s, 3H). LRMS m/z (M+H) Calcd: 324.0, found: 324.0.

Provenance & Evidence