Thionyl Chloride → 6-Cyanopyridine-3-sulfonyl chloride

SOCl2 (1.8 ml, 24.8 mmol) was added dropwise to ice water and stirred for 18 h at room temperature. CuCl2 (22 mg, 0.22 mmol) was added at 0° C. and the mixture was stirred for 15 min. In a separate flask, a solution of NaNO2 (450 mg, 6.52 mmol) in water (4.5 ml) was added to a stirred solution of 5-amino-pyridine-2-carbonitrile (534 mg, 4.5 mmol) in conc. HCl (4.5 ml) at 0° C., over 15 min. The diazonium salt solution was added dropwise to the thionyl chloride/CuCl2 solution at 0° C. and stirring was continued for 1 h. The reaction mixture was extracted with DCM and the combined organic phases were dried (Na2SO4) and concentrated in vacuo to give the title compound (620 mg) which was used in the next step without purification. The structure was confirmed by 1H NMR.

1. stirringthe mixture was stirred for 15 min
2. stirringstirring
3. waitwas continued for 1 h
4. extractionThe reaction mixture was extracted with DCM
5. dry with materialthe combined organic phases were dried (Na2SO4)
6. concentrationconcentrated in vacuo

ORD record

ord-ea9796652c8b4e24a25a9a7da0e40a4e

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102688B2