Potassium Phosphate, Tribasic → 1-[1-(9-Methyl-8-pyridin-3-yl-9H-purin-6-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of pyridin-3-ylboronic acid (50 mg, 0.41 mmol, Maybridge) in dioxane (0.75 mL) and water (0.1 mL) were added 1-(1-(8-bromo-9-methyl-9H-purin-6-yl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one (50 mg, 0.12 mmol), Pd(dppf)Cl2 (20 mg, 0.02 mmol), and tribasic potassium phosphate (75 mg, 0.36 mmol). The reaction mixture was heated in a microwave reactor to 150° C. for 20 min. The product was purified by preparatory HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid) to give 15 mg (29.3% yield) of the title compound. 1H NMR (400 MHz, DMSO-d6): δ 10.84 (s, 1H), 9.03 (m, 1H), 8.72 (dd, 1H), 8.32 (m, 1H), 8.25 (m, 1H), 7.59 (ddd, 1H), 7.15 (m, 1H), 6-91 (m, 3H), 4.55 (t, 1H), 3.85 (s, 3H), 2.35 (m, 2H), 1.84 (d, 2H); MS (EI) for C23H22N8O: 427.4 (MH+).

Provenance & Evidence