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

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).

1. washwashed with 10% Na2CO3 (50 mL)
2. dry with materialwater (50 mL) and finally brine (50 mL) and dried over sodium sulfate
3. customThe solvents were evaporated at reduced pressure
4. customto give a thick oily solution
5. washthe solution was washed with 0.1M sodium thiosulfate (75 mL), brine (50 mL)
6. dry with materialdried over sodium sulfate
7. customThe solvents were evaporated at reduced pressure
8. customthe residual oil was purified by silica gel chromatography

ORD record

ord-11de137c370a4308a60f262e8af1e645

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181223B2