Sodium Carbonate → 2-Formyl-6-naphthylpyridine

Participants

Reaction Conditions

Reaction Steps

Inside of a dry box, naphthylboronic acid (9.12 g, 53.0 mmol) and Na2CO3 (11.64 g, 110 mmol) are dissolved in 290 mL of degassed 4:1 H2O/MeOH. This solution is added to a solution of 8 g (43 mmol) of 2-bromo-6-formylpyridine and 810 mg (0.7 mmol) of Pd(PPh3)4 in 290 mL of degassed toluene. The charged reactor is removed from the dry box, while under a blanket of N2 and is connected to the house N2 line. The biphasic solution is vigorously stirred and heated to 70° C. for 4 h. On cooling to RT, the organic phase is separated. The aqueous layer is washed with 3×75 mL of Et2O. The combined organic extracts are washed with 3×100 mL of H2O and 1×100 mL of brine and dried over Na2SO4. After removing the volatiles in vacuo, the resultant light yellow oil is purified via trituration with hexanes. The isolated material is recrystallized from a hot hexane solution and ultimately yielded 8.75 g, 87% yield. mp 65–66° C.

Provenance & Evidence