Potassium Carbonate → 5'-(3-Chlorophenyl)-4-methoxy-5''-methyldispiro[cyclohexane-1,2'-[1]-benzofuran-3',2''-imidazol]-4''-amine

Participants

Reaction Conditions

Reaction Steps

3-Chlorophenylboronic acid (47.7 mg, 0.31 mmol), 5′-bromo-4-methoxy-5″-methyldispiro-[cyclohexane-1,2′-[1]benzofuran-3′,2″-imidazol]-4″-amine (Example 29, 77 mg, 0.20 mmol) and (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(I) (8.37 mg, 10.18 μmol) were put in a microwave vial and dissolved in dry dioxane (2 mL). A 2M aq. solution of K2CO3 (0.204 mL, 0.41 mmol) was added, the mixture was degassed with nitrogen gas and the mixture was heated at 120° C. for 20 min in a microwave reactor. The mixture was combined with a second reaction from 10 mg (0.03 mmol) of 5′-bromo-4-methoxy-5″-methyldispiro[cyclohexane-1,2′-[1]benzofuran-3′,2″-imidazol]-4″-amine and concentrated. EtOAc (7 mL) and a sat. aq. solution of NaHCO3 (5 mL) was added and the phases were separated. The aqueous phase was extracted with EtOAc (5 mL) and the combined organic layers were dried over MgSO4, filtered and evaporated. The crude product was purified by preparative chromatography, yielding 38.5 mg of the title compound (41% yield). 1 H NMR (500 MHz, DMSO-d6) δ ppm 1.21 (m, 1 H), 1.46 (m, 3 H), 1.82 (m, 2 H), 1.98 (m, 2 H), 2.21 (s, 3 H), 3.09 (m, 1 H), 3.22 (s, 3 H), 6.71 (br. s., 2 H), 6.85 (d, 1 H), 6.98 (d, 1 H), 7.32 (m, 1 H), 7.40 (s, 1 H), 7.47 (m, 1 H), 7.51 (m, 1 H), 7.54 (s, 1 H); MS (APCI+) m/z 410 [M+H]+.

Provenance & Evidence