Cesium carbonate → HCID 66892777, compound

Participants

Reaction Conditions

Reaction Steps

Xylene (150 mL) was added to 7-iodo-5-nitro-1-benzofuran (1.00 g, 3.46 mmol), octahydrothieno[3,4-b]pyrazine 6,6-dioxide (0.73 g, 4.15 mmol; Intermediate 34), Pd2(dba)3 (0.08 g, 0.87 mmol), Xantphos (0.20 g, 0.35 mmol) and Cs2CO3 (1.59 g, 4.84 mmol). The resulting mixture was stirred at 120° C. overnight, filtered through Celite and the solvent was removed in vacuo. The crude product was purified by flash chromatography [eluent: DCM and DCM:MeOH (1:1)] and then recrystallized from MeOH to afford 0.354 g (8%) of the title product. HPLC 90%, RT: 1.390 (System A; 10-97% MeCN over 3 min). 1H NMR (270 MHz, CDCl3) δ ppm 2.85 (dd, J=12.62, 7.42 Hz, 1H) 3.16-3.49 (m, 6H) 3.71 (t, J=11.63 Hz, 1H) 4.02-4.05 (m, 1H) 5.17-5.25 (m, 1H) 6.93 (d, J=2.23 Hz, 1H) 7.62 (t, J=2.72 Hz, 1H) 7.77 (d, J=1.98 Hz, 1H) 8.19 (d, J=1.98 Hz, 1H). LC-MS 338 (M+H)+.

Provenance & Evidence