4-Bromobenzoic acid → HCID 118357283, compound

Participants

Reaction Steps

4-Bromobenzoic acid (1, 685.0 mg, 3.4 mmol) and HATU (1298.1 mg, 3.4 mmol) are partially dissolved in DMF (10 mL) at rt. DIEA (560 μL, 3.4 mmol) is added to this mixture to give a pale yellow solution. After stirring at rt for 30 min, tert-butyl 4-(4-aminobenzyl)piperazine-1-carboxylate (2, 992.9 mg, 3.4 mmol) is added and the resulting reaction mixture is heated at 60° C. for 20 h, allowed to cool to rt, and poured into water (100 mL). This mixture is extracted with Et2O (3×150 mL). The combined organic extracts are evaporated to dryness to give a white solid, which is washed with water (50 mL) and dried in vacuo. This material is used in the next synthetic step without further purification. HPLC: tR 1.67 min (method 1). LC-MS m/z calcd for C23H2879BrN3O3 ([M]+), 473. found, 474 ([M+H]+). 1H NMR (CD3OD): δ 1.46 (s, 9H), 2.96 (m, 4H), 3.59 (m, 4H), 4.05 (br s, 2H), 7.46 (m, 2H), 7.69 (m, 2H), 7.78 (m, 2H), 7.85 (m, 2H).

Provenance & Evidence