Thionyl Chloride → HCID 89996174, compound

To a stirred solution of (6-chloro-3-iodo-pyridin-2-yl)-methanol (2.5 g, 9.3 mmol, 1 eq) in DCM (25 mL) was added thionyl chloride (0.68 mL, 9.3 mmol, 1 eq) in drop wise manner at 0° C. under nitrogen atmosphere. Resulting reaction mixture was stirred at room temperature for 16 hours. After complete consumption of starting material, reaction mixture was cooled to 0° C. and quenched by aqueous sodium bicarbonate (25 mL), extracted with DCM (3×70 mL). Combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure to get brown semisolid (2.5 g, crude). Crude title compound was used as such for the next reaction. 1H NMR not clean. LC-MS: No ionization.

1. customResulting
2. customreaction mixture
3. customAfter complete consumption of starting material, reaction mixture
4. temperaturewas cooled to 0° C.
5. customquenched by aqueous sodium bicarbonate (25 mL)
6. extractionextracted with DCM (3×70 mL)
7. dry with materialCombined organic phase was dried over anhydrous Na2SO4
8. concentrationconcentrated under reduced pressure
9. customto get brown semisolid (2.5 g, crude)

ORD record

ord-0796a9d1e17b482c94780890e10c49fe

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09131697B2