Triethylamine → HCID 12093792, compound

Participants

Reaction Steps

A 25-mL round bottom flask equipped with a stir bar was charged with 6 (180 mg, 0.46 mmol) and CH2Cl2 (5.0 mL). The reaction mixture was treated with boronic acid 7 (135 mg, 0.92 mmol), Et3N (0.13 mL, 0.92 mmol), crushed 4 A mol. sieves (720 mg, 4× weight) and Cu(OAc)2 (167 mg, 0.92 mmol) at 25° C. After 12 h, the reaction was filtered through a plug of Celite® and washed with CH2Cl2 (100 mL). The organic phase was washed with brine (50 mL), dried (Na2SO4), filtered, and concentrated in vacuo. Chromatography of the residue on silica (40-50% EtOAc/hexanes) provided 8 (100 mg, 44%) as a white solid: ESI-MS m/z: [C28H23N5O2S+H]+ 494; 1H NMR (300 MHz, CDCl3) δ 7.90-7.00 (m, 13H), 4.19 (t, J 7.5 Hz, 2H), 2.33 (s, 3H), 1.99-1.85 (m, 2H), 1.03 (t, J=7.3 Hz, 3H).

Provenance & Evidence