Sodium Carbonate → Methyl 2-(4-fluorophenyl)nicotinate

Participants

Reaction Conditions

Reaction Steps

To a nitrogen purged flask was charged Pd(Ph3)4 (1.84 g, 1.6 mmoles, 0.005 eq), sodium carbonate (42.8 g, 404 mmoles, 1.3 eq), 52 (55.5 g, 320.6 mmoles, 1.0 eq), p-fluorophenylboronic acid (53.8 g, 384.7 mmoles, 1.2 eq), followed by 1.3 L denatured EtOH. The reaction was heated to 78° C. with vigorous stirring under N2 overnight. HPLC analysis [Tret 52=10 min, Tret 54=12 min] of the reaction mixture showed that the starting material was completely consumed and a later-eluting peak produced. The reaction was cooled to room temperature and the solvents removed under vacuum. The residue was dissolved in EtOAc, washed, dried (MgSO4), filtered through celite, and concentrated to afford a pale yellow solid 54.

Provenance & Evidence