Sodium Iodide → HCID 46177179, compound

Temperature

90 °C

6-Chloro-pyridine-2-carbonitrile (5.0 g, 36 mmol) was taken up in propionitrile (35 mL). To this was added TMSCl (4.6 mL, 36 mmol) and sodium iodide (16.0 g, 108 mmol) and the solution was heated to 90° C. for 16 h. The solution was cooled and quenched by the addition of 2M sodium hydroxide (35 mL) The mixture was extracted with ethyl acetate (3×30 mL) and washed with water (1×50 mL) and saturated aqueous sodium bisulfate. The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (silica-gel) using 0-100% ethyl acetate in hexanes to afford 4.6 g of the title compound.

1. temperatureThe solution was cooled
2. customquenched by the addition of 2M sodium hydroxide (35 mL) The mixture
3. extractionwas extracted with ethyl acetate (3×30 mL)
4. washwashed with water (1×50 mL) and saturated aqueous sodium bisulfate
5. dry with materialThe combined organic layers were dried over sodium sulfate
6. concentrationconcentrated
7. customThe residue was purified by flash chromatography (silica-gel)

ORD record

ord-b0b195885cc44830a3adf7f9fe5b1faf

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481750B2