Nitrogen → HCID 51348522, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (1S,2S)-2-thiophen-2-yl-cyclopropanecarboxylic acid [(R)-1-(4-bromo-phenyl)-2-hydroxy-ethyl]-amide (560 mg, 1.53 mmol), K3PO4 (650 mg, 3.0 mmol)) and p-tolylboronic acid (310 mg, 2.3 mmol) in DME/H2O (3/1, 2 ml) was passed through N2 and then Pd(PPh3)4 (178 mg, 0.153 mmol) added. The mixture was stirred in a sealed tube at 85° C. for 1.5 h. The reaction mixture was poured 1N NaOH and extracted with EtOAc (3×). The combined EtOAc layer was dried over MgSO4. After removal of the solvent, the residue was subjected to silica column (50% EtOAc in DCM and then 10% MeOH in DCM). The product obtained was further purified by crystallization (iPrOH/EtOAc) and Prep HPLC to give the titled compound (275 mg). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.6 (d, J=8.1 Hz, 2H), 7.5 (d, J=7.8 Hz, 2H), 7.4 (d, J=8.1 Hz, 2H), 7.2 (d, J=7.6 Hz, 2H), 7.1 (t, J=5.4 Hz, 1H), 6.8-7.0 (m, 2H), 5.0 (dd, J=5.4, 1.9 Hz, 1H), 3.7-3.8 (m, 2H), 2.5-2.7 (m, 1H), 2.4 (s, 3H), 2.1 (t, J=8.7 Hz, 1H), 1.4-1.6 (m, 1H), 1.2 (ddd, 1H). LRMS (ESI)=378, [(M+1)+ calcd for C23H24NO2S 377.5].

Provenance & Evidence