N-Iodosuccinimide → 7-Chloro-3-iodoimidazo[1,2-a]pyridine

To a solution of 7-Chloro-imidazo[1,2-a]pyridine (30.9 g, 186 mmol, 1.0 equiv) in DMF (280 ml) was added N-iodosuccinimide (43.6 g, 194 mmol, 1.05 equiv) and the resulting mixture was stirred overnight at RT. The thin brown slurry was diluted with water (840 ml), brine (280 ml) and extracted with EtOAc (560 ml). The aqueous layer was further extracted with EtOAc (3×280 ml). The combined organic phases were washed with water (2×280 ml), 10% w/v sodium thiosulfate (280 ml), brine (280 ml), dried (MgSO4), filtered and concentrated in vacuo to give a brown residue. The residue was triturated with ether (200 ml), filtered and the solid was washed with ether (2×50 ml) and dried on the filter to give 39 g of product. MS: [M+H]+=279.

1. extractionextracted with EtOAc (560 ml)
2. extractionThe aqueous layer was further extracted with EtOAc (3×280 ml)
3. washThe combined organic phases were washed with water (2×280 ml), 10%
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto give a brown residue
8. customThe residue was triturated with ether (200 ml)
9. filtrationfiltered
10. washthe solid was washed with ether (2×50 ml)
11. customdried on the
12. filtrationfilter

ORD record

ord-8ff507bd68164d4dbb819641187afda9

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796244B2