3-Bromo-5-iodopyridine → HCID 86679137, compound

Temperature

-78 °C

To a solution of 3-bromo-5-iodopyridine (0.14 g, 0.493 mmol) in THF (2 mL) cooled at −78° C. was added nBuLi (462 μl, 0.74 mmol) dropwise over 5 min. The reaction mixture was stirred at −78° C. for 15 min, then (R)-2-methyl-N-(oxetan-3-ylidene)-propane-2-sulfinamide (0.1 g, 0.567 mmol) in THF (1 mL) was added dropwise. The reaction mixture was stirred at −78° C. for 10 min then allowed to warm up to RT. The mixture was quenched with water (2 mL) and extracted with EtOAc (2×10 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 100% EtOAc-heptane gradient to give the title compound (0.096 g, 58%) as a light yellow oil. MS: 333.0 and 335.1 (M+H+).

1. stirringThe reaction mixture was stirred at −78° C. for 10 min
2. temperatureto warm up to RT
3. customThe mixture was quenched with water (2 mL)
4. extractionextracted with EtOAc (2×10 mL)
5. dry with materialCombined organics were dried over Na2SO4
6. filtrationfiltered
7. customevaporated to dryness
8. customThe residue was purified by silica gel flash chromatography
9. washeluting with a 0 to 100% EtOAc-heptane gradient

ORD record

ord-25092a209d824649be2e3f0e0b3e12b0

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260408B2