5-Methyl-2-(tri-n-butylstannyl)pyridine → 1-methyl-2-(1-(2-methyl-6-(5-methylpyridin-2-yl)pyrimidin-4-yl)azetidin-3-yl)-1H-benzo[d]imidazole

Participants

Reaction Conditions

Reaction Steps

To a microwave vial was added 5-methyl-2-(tributylstannyl)pyridine (97 mg, 2.6 mmol), Intermediate 3 (40 mg, 0.13 mmol), tetrakis(triphenylphosphine)palladium(0) (15 mg, 0.013 mmol), and DMF (1 mL). The vial was sealed and heated in a heating block at 110° C. for 16 h. The reaction was cooled to room temperature, passed through a syringe filter, and purified by reverse-phase chromatography (5-55% acetonitrile/water/0.1% TFA). The product fractions were poured into aqueous NaHCO3 and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, and concentrated to give Example 94 as a white solid. 1H NMR: (400 MHz, CDCl3) δ 8.50 (s, 1H), 8.28 (d, J=8.0 Hz, 1H), 7.75 (d, J=7.3 Hz, 1H), 7.61 (d, J=8.0 Hz, 1H), 7.29 (m, 3H), 7.15 (s, 1H), 4.66 (m, 4H), 4.29 (m, 1H), 3.74 (s, 3H), 2.60 (s, 3H), 2.40 (s, 3H) ppm. MS: m/z=371.5 (M+H).

Provenance & Evidence