Iodine → 3,5-Dichloro-4-iodopyridine

To a stirred solution of 3,5-dichloropyridine (3.0 g, 20.4 mmol) in THF (15 mL) was added LDA (2.0 M solution in THF/heptane/ethylbenzene, 12.14 mL, 24.4 mmol) dropwise at 0° C. and the mixture was stirred at the same temperature for 1 h. A solution of iodine (2.7 g, 21.4 mmol) in THF (10 mL) added dropwise to above mixture. Upon completion of addition, the mixture was stirred at the same temperature for 1 h. The reaction mixture was quenched with water (40 mL) and extracted with EtOAc (4×50 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to provide compound B15-1 (3.2 g, 57%) as a yellow gum.

1. additionUpon completion of addition
2. stirringthe mixture was stirred at the same temperature for 1 h
3. customThe reaction mixture was quenched with water (40 mL)
4. extractionextracted with EtOAc (4×50 mL)
5. washThe combined organic layers were washed with brine (50 mL)
6. dry with materialdried over anhydrous Na2SO4
7. concentrationconcentrated under reduced pressure
8. customto provide compound B15-1 (3.2 g, 57%) as a yellow gum

ORD record

ord-9dca1dc0dd5a4c709611a7f02791972a

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365522B2