Cesium carbonate → 1-Methyl-2-(1-(2-methyl-6-(2-methylpyridin-3-yl)pyrimidin-4-yl)azetidin-3-yl)-1H-benzo[d]imidazole

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Reaction Conditions

Reaction Steps

A solution of Intermediate 3 (0.015 g, 0.048 mmol), (2-methylpyridin-3-yl)boronic acid (9.9 mg, 0.072 mmol), and cesium carbonate (1 M, 0.12 mL, 0.12 mmol) in THF (0.5 mL) under an atmosphere of nitrogen was treated with bis(tri-tert-butylphosphine)palladium(0) (1.5 mg, 0.0029 mmol) and heated to 100° C. overnight. The mixture was cooled, stirred with Quadrapure for 3 h, filtered, and concentrated. The residue was purified by reverse phase HPLC to give Example 80. 1H NMR: (400 MHz, d6-DMSO) δ 8.68 (d, J=1.2 Hz, 1H), 7.91 (d, J=15.0 Hz, 1H), 7.68-7.63 (m, 2H), 7.51-7.48 (m, 1H), 7.35-7.27 (m, 2H), 6.83 (s, 1H), 4.79-4.74 (m, 2H), 4.65-4.56 (m, 3H), 3.80 (s, 3H), 2.56 (s, 3H), 2.53 (s, 3H). MS: m/z=371.4 (M+H).

Provenance & Evidence