Potassium Iodide → 2-Chloro-4-((6-iodopyridin-3-yl)oxy)pyridine

関与物質

反応手順

A mixture of 5-((2-chloropyridin-4-yl)oxy)pyridin-2-amine (1.00 g, 4.51 mmol) and potassium iodide (3.74 g, 22.5 mmol) in DCM (15 mL) was treated dropwise with t-butyl nitrite (4.65 g, 45.1 mmol) and the mixture was stirred overnight at RT. The mixture was diluted with EtOAc (75 mL) and washed with 10% Na2CO3 (50 mL), then water (50 mL) and finally brine (50 mL) and dried over sodium sulfate. The solvents were evaporated at reduced pressure to give a thick oily solution. EtOAc (100 mL) was added and the solution was washed with 0.1M sodium thiosulfate (75 mL), brine (50 mL) and dried over sodium sulfate. The solvents were evaporated at reduced pressure, and the residual oil was purified by silica gel chromatography to provide 2-chloro-4-((6-iodopyridin-3-yl)oxy)pyridine (695 mg, 46%). 1H NMR (400 MHz, DMSO-d6): δ 8.80 (d, J=3.0 Hz, 1H), 8.73 (d, J=5.8 Hz, 1H), 8.35 (d, J=8.6 Hz, 1H), 7.91 (dd, J=8.6, 3.1 Hz, 1H), 7.61 (d, J=2.3 Hz, 1H), 7.48 (dd, J=5.8, 2.3 Hz, 1H).

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