Cesium carbonate → 6-Chloro-1-methyl-N-(5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-yl)-1H-benzo[d]imidazol-4-amine

Participants

Reaction Conditions

Reaction Steps

A microwave vial equipped with a magnetic stirrer was charged with 109d (486 mg, 2.0 mmol), 5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-amine (390 mg 1.67 mmol), cesium carbonate (1.09 g, 3.34 mmol), tris(dibenzylideneacetone)dipalladium(0) (152 mg, 0.167 mmol) and Xantphos (193 mg, 0.334 mmol). After bubbling nitrogen through the suspension for 5 minutes, the reaction was heated at 120° C. for overnight. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was washed with a mixture of petroleum ether/ethyl acetate (15 mL, 2:1) to afford 109e as a yellow solid (720 mg, 100%). LCMS: [M+H]+ 399.3. 1H NMR (500 MHz, CDCl3) δ 8.20 (d, J=2.0, 1H), 8.04 (d, J=2.5, 1H), 7.72 (s, 1H), 7.61 (s, 1H), 7.28-7.29 (m, 1H), 6.90-6.91 (m, 2H), 4.70-4.71 (m, 4H), 3.77 (s, 3H), 3.70-3.71 (m, 1H), 3.17 (t, J=5.0, 4 H), 2.52 (t, J=5.0, 4H)

Provenance & Evidence