Potassium Carbonate → N-isobutyl-2-methyl-2-(4-(1-methyl-1H-pyrrol-2-yl)phenyl)propanamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-isobutyl-2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanamide (example 23a) (19.04 g, 55.14 mmol), K2CO3 (22.86 g, 165.4 mmol), and N-methyl-2-bromopyrrole (7.50 g, 93.74 mmol) in DME/H2O (4/1, 300 mL) was added Pd(PPh3)4 (3.20 g, 2.76 mmol) at RT under argon and the reaction mixture was stirred at 85° C. overnight. After it was cooled down to room temperature, the reaction mixture was diluted with brine, and extracted with EtOAc (3×). The combined organic layers were washed with brine, and dried over Na2SO4. After evaporation of the solvent under reduced pressure, the residue was purified twice by chromatography on silica gel eluting with EtOAc/Hexanes (1/9) to give the title compound as off-white white solid, which was further purified by recrystallization from hexanes, and dried under vacuum overnight. mp: 59-60° C. 1H NMR (400 MHz, DMSO-d6) δ 7.35 (d, J=7.2 Hz, 2H), 7.31 (d, J=7.2 Hz, 2H), 6.79 (m, 1H), 6.09 (m, 1H), 6.01 (m, 1H), 3.60 (s, 3H), 2.82 (t, J=6.4 Hz, 2H), 1.7 (m, 1H), 1.44 (s, 6H), 0.2 (d, J=7.2 Hz, 6H). MS 299 (MH+).

Provenance & Evidence