Sodium Carbonate → HCID 68538250, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 250 mg (0.704 mmol) 4-(4-amino-3-bromo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (as prepared in Example 61, step (c)) in 6 mL toluene and 3 mL EtOH was treated with 119 mg (0.774 mmol) 4,4-dimethyl-cyclohex-1-enylboronic acid and 2.81 mL (5.63 mmol) 2.0 M Na2CO3. The mixture was degassed via sonication, placed under Ar, treated with 56.9 mg (0.0493 mmol) Pd(PPh3)4, and heated to 85° C. for 27 h and allowed to stand at RT for 36 h. The mixture was diluted with EtOAc (15 mL) and washed with water (1×15 mL). The combined aqueous layers were extracted with EtOAc (15 mL), and the combined organic layers were dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue on a Varian MegaBond Elut 50-gm column with 10-15% EtOAc-hexane afforded 89.0 mg (33%) of the title compound as a tan solid: Mass spectrum (ESI, m/z): Calcd. for C20H29N2O2, 329.2 (M—C4H9+2H), found 329.2.

Provenance & Evidence