Cesium carbonate → HCID 63962346, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,4-difluorophenol (1.55 g, 11.9 mmol), 2,6-dibromopyridine (2.82 g, 11.9 mmol), and Cs2CO3 (3.88 g, 11.9 mmol) in N-Methyl-2-pyrrolidinone (10 mL) was stirred at 100° C. for 18 h, then was cooled to rt. EtOAc (10 mL) and 1N aq. NaOH (20 mL) were added to the reaction mixture. The organic layer was separated and washed with water (3×) and brine, dried (MgSO4), and filtered. The filtrate was concentrated in vacuo. The crude product was chromatographed (SiO2; continuous gradient of EtOAc/hexanes from 0% to 10% over 12 min) to give the title compound (2.90 g, 10.1 mmol, 85% yield) as a clear oil, which eventually became a white solid. 1H NMR (CDCl3) δ: 7.56 (t, J=7.8 Hz, 1H), 7.24 (d, J=7.5 Hz, 1H), 7.18 (q, J=9.1 Hz, 1H), 7.06-7.00 (m, 1H), 6.92-6.87 (m, 1H), 6.85 (d, J=8.1 Hz, 1H); 19F NMR (CDCl3) δ: −134.55 (d, J=21.4 Hz), −142.14 (d, J=21.3 Hz).

Provenance & Evidence