Potassium Carbonate → N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(1,4-dimethyl-1H-imidazol-2-yl)phenethoxy)propanamide

Participants

Reaction Conditions

Reaction Steps

N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethoxy)propanamide [Example 34, Step i)] (390 mg), potassium carbonate (220 mg), Pd(Ph3P)4 (46 mg) and 2-bromo-1,4-dimethyl-1H-imidazole (279 mg) in MeOH (3 mL) was loaded into a microwave vial, flushed with nitrogen and sealed. The vial was heated within a Discover microwave at 120° C. for 30 min. After cooling, the reaction and the filtrate washed with DCM. Volatiles were removed and the residue purified on silica using 20%-100% EtOAc/iso gradient to afford the subtitled compound (358 mg). MS [M+H]+=458 (MultiMode+) 1H NMR (400 MHz, CDCl3) δ 7.51-7.47 (m, 1H), 7.43-7.40 (m, 1H), 7.37-7.30 (m, 1H), 7.27-7.22 (m, 1H), 6.67 (s, 1H), 4.61 and 4.37 (2×t, J=5.2 Hz, 1H), 4.25-4.16 and 3.61-3.51 (2×m, 1H), 3.81-3.74 (m, 2H), 3.73-3.65 (m, 2H), 3.68 (s, 3H), 3.41 (s, 3H), 3.39 (s, 3H), 3.37 and 3.29 (2×d, J=4.9 Hz, 2H), 2.96-2.89 (m, 2H), 2.73-2.65 (m, 2H), 2.26 (s, 3H), 1.85-1.74 (m, 2H), 1.73-1.05 (m, 8H); a ˜2:1 mixture of rotamers is observed.

Provenance & Evidence