Potassium Carbonate → Tert-butyl 3-methyl-4-[(5-nitro-1-benzofuran-7-yl)methyl]piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-(bromomethyl)-5-nitro-1-benzofuran (120 mg, 70 mol %, 0.39 mmol; Intermediate 64), K2CO3 (162 mg, 1.17 mmol) and tert-butyl 3-methylpiperazine-1-carboxylate (94 mg, 0.47 mmol) in dry MeCN (5 mL) was heated at 80° C. while stirring for 1 h 45 min using a StemBlock. The solvent was evaporated under reduced pressure and the residue was partitioned between water and DCM (×2). The organic layers were combined, dried (Na2SO4) and purified using flashtube (10% MeOH in DCM). This afforded the title product (115 mg, 78%) as a light yellow sticky oil. HPLC 99%, RT=2.47 min (System A; 5-60% MeCN over 3 min), 99%, RT=2.27 min (System B; 5-60% MeCN over 3 min). MS (ESI+) for C19H25N3O5 m/z 376 (M+H)+.

Provenance & Evidence