Trimethylsilyl iodide → N-(6-(3-chloro-2-oxo-1,2-dihydropyridin-4-yl)-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

Participants

Reaction Steps

To N-(3′-chloro-2′-methoxy-3-methyl-2,4′-bipyridin-6-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (71 mg, 0.15 mmol) in chloroform (2 mL) was added iodotrimethylsilane (90 mg, 0.45 mmol). The reaction mixture was stirred at room temperature for six hours. The reaction mixture was evaporated to dryness and purified by reverse phase preparative liquid chromatography to yield the product as a trifluoroacetic acid salt. The salt was dissolved in dichloromethane (5 mL) and washed with a saturated sodium bicarbonate solution (2×5 mL). The organics were dried over sodium sulfate and evaporated to yield the product (23 mg, 33%). ESI-MS m/z calc. 459.08. found 460.3 (M+1)+. Retention time 1.11 minutes. 1H NMR (400 MHz, DMSO-d6) δ 12.26 (s, 1H), 9.11 (s, 1H), 7.97 (d, J=8.5 Hz, 1H), 7.75 (d, J=8.6 Hz, 1H), 7.55 (m, 1H), 7.44 (d, J=6.6 Hz, 1H), 7.40-7.38 (m, 1H), 7.35-7.32 (m, 1H), 6.11 (d, J=6.6 Hz, 1H), 2.06 (s, 3H), 1.51-1.50 (m, 2H), 1.17-1.15 (m, 2H).

Provenance & Evidence