Cesium carbonate → HCID 59239861, compound

Participants

Reaction Conditions

Reaction Steps

To a 350 mL high-pressure vial was added ethyl 4-bromobenzoate (12.92 g, 56.4 mmol), t-butyl carbazate (14.91 g, 112.8 mmol), Pd2(dba)3 (0.516 g, 0.56 mmol), dppf (0.938 g, 1.69 mmol), Cs2CO3 (18.4 g, 56.4 mmol), and dry toluene (113 mL). The reaction mixture was degassed for 5 min, sealed and heated to 100° C. for 16 h. The completion of the reaction was monitored by analytical HPLC. The reaction mixture was allowed to cool to room temperature, diluted with DCM, filtered and the filtrate was concentrated. The crude was then purified by flash chromatography (AcOEt/Hexane (0→30%) to afford the desired product. ESI-MS (m/z): 265 [M+H—NH3]+, 225 [M+H-tBu]+, 181 [M+H-Boc]+. 1H NMR (400 MHz, DMSO-d6): δ (ppm) 1.31 (t, J=7.1 Hz, 3H, CH3 ethyl), 1.50 (s, 9H, CH3 Boc), 4.28 (q, J=7.1 Hz, 2H, CH2 ethyl), 5.14 (s, 2H, NH2), 7.70 (dt, J=8.8, 2.2 Hz, 2H, H2 and H6 phenyl), 7.87 (dt, J=8.8, 2.2 Hz, 2H, H3 and H5 phenyl).

Provenance & Evidence