Potassium Carbonate → 7'-(5-Chloropyridin-3-yl)-5''-methyl-3',4'-dihydrodispiro[cyclopropane-1,2'-naphthalene-1',2''-imidazol]-4''-amine

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Reaction Conditions

Reaction Steps

A mixture of 7′-bromo-5″-methyl-3′,4′-dihydrodispiro[cyclopropane-1,2′-naphthalene-1′,2″-imidazol]-4″-amine (Example 1, 100 mg, 0.31 mmol), 5-chloropyridin-3-ylboronic acid (74 mg, 0.47 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride (23 mg, 0.03 mmol), aq. potassium carbonate (2 M, 0.31 mL, 0.63 mmol) and 1,4-dioxane (1 mL) were mixed in a vial and heated in a microwave reactor at 130° C. for 30 min. When cooled to r.t., the mixture was diluted with DCM, washed with water and dried over Na2SO4. The filtrate was concentrated and the product purified by preparative HPLC to give the title compound (41 mg, 37% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.10 (m, 2 H), 0.24 (m, 1 H), 0.55 (m, 1 H), 1.51 (dt, 1 H), 2.18 (s, 3 H), 2.39 (m, 1 H), 3.01 (m, 2 H), 6.52 (br. s., 2 H), 6.74 (d, 1 H), 7.30 (d, 1 H), 7.52 (dd, 1 H), 7.97 (s, 1 H), 8.57 (d, 1 H), 8.61 (d, 1 H); MS (APCI+) m/z 351 [M+H]+.

Provenance & Evidence