Dimethylformamide → HCID 58318794, compound

Participants

Reaction Steps

A mixture of polymer-bound triphenylphosphine (18 mg, 0.047 mmol, 0.15 eq) and palladium(II) acetate (5.0 mg, 0.022 mmol, 0.07 eq) in DMF (1.0 mL) stirred under argon at rt for 2 h. The supernatant DMF was removed, and fresh DMF (1.0 mL) was added. Methyl 3-bromo-5-(pyrimidin-5-yloxy)benzoate (96 mg, 0.31 mmol, 1.0 eq) and zinc cyanide (37 mg, 0.31 mmol, 1.0 eq) were added, and the vial was subjected to microwave irradiation at 150° C. for 25 minutes. The resin was washed with ether, and the collected filtrate was washed (3×) with water and (1×) with brine. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 25 mg (32%) of the title compound as a clear oil: 1H NMR (400 MHz, DMSO-d6) δ 9.09 (s, 1H), 8.76 (s, 2H), 8.16 (s, 1H), 8.07 (dd, J=2.3, 1.3 Hz, 1H), 7.91 (dd, J=2.3, 1.4 Hz, 1H), 3.88 (s, 3H); ES-MS [M+1]+:256.1.

Provenance & Evidence