Dimethylformamide → HCID 67307527, compound

Participants

Reaction Steps

A mixture of polymer-bound triphenylphosphine (170 mg, 0.437 mmol, 0.150 eq) and palladium(II) acetate (46 mg, 0.20 mmol, 0.070 eq) in DMF (8.7 mL) stirred under argon for 2 h at rt. The supernatant DMF was removed, and fresh DMF (8.7 mL) was added. Compound 20 (1.0 g, 2.9 mmol, 1.0 eq) and zinc cyanide (340 mg, 2.90 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 330 mg (47%) of the title compound as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 9.20 (s, 1H), 8.63 (s, 2H), 8.32 (t, J=1.4 Hz, 1H), 8.07 (t, J=2.2 Hz, 1H), 7.62 (dd, J=2.3, 1.3 Hz, 1H); ES-MS [M+1]+:243.0.

Provenance & Evidence