Dimethylformamide → HCID 58349269, compound

Participants

Reaction Steps

A mixture of polymer-bound triphenylphosphine (230 mg, 0.597 mmol, 0.150 eq) and palladium(II) acetate (63 mg, 0.28 mmol, 0.070 eq) in DMF (12 mL) stirred under argon at rt for 2 h. The supernatant DMF was removed, and fresh DMF (12 mL) was added. Compound 4 (1.0 g, 3.9 mmol, 1.0 eq) and zinc cyanide (470 mg, 4.00 mmol, 1.00 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 780 mg (100%) of the title compound as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 8.84 (d, J=1.4 Hz, 1H), 8.74 (d, J=2.8 Hz, 1H), 8.51 (d, J=2.8 Hz, 1H), 8.47 (d, J=4.6 Hz, 1H), 8.13 (t, J=2.1 Hz, 1H), 7.63 (ddd, J=8.4, 2.7, 1.1 Hz, 1H), 7.49 (dd, J=8.5, 4.6 Hz, 1H); ES-MS [M+1]+:198.1.

Provenance & Evidence