Sodium Carbonate → 2-[4-Amino-3-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-ethanesulfonic acid tert-butyl amide

Participants

Reaction Conditions

Reaction Steps

A solution of 380 mg (1.13 mmol) of 2-(4-amino-3-bromo-phenyl)-ethanesulfonic acid tert-butylamide (as prepared in Example 47, step (a)) in toluene (10 mL) and EtOH (5 mL) was treated with 321 mg (1.36 mmol) of 4,4-dimethylcyclohex-1-enylboronic acid and 4.53 mL (9.06 mmol) of 2.0 M aqueous Na2CO3. The mixture was degassed via sonication, placed under Ar, treated with 131 mg (0.113 mmol) of Pd(PPh3)4, and heated to 80° C. for 19 h. The mixture was diluted with EtOAc (30 mL) and washed with water (1×20 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue on a 50-g Varian MegaBond Elut SPE column with 1% MeOH—CH2Cl2 afforded 267 mg (64%) of the title compound as an off-white solid: Mass spectrum (ESI, m/z): Calcd. for C20H32N2O2S, 365.2 (M+H), found 365.2.

Provenance & Evidence