Isopropyl iodide → HCID 59541857, compound

To a stirred solution 5-iodopyridin-2-ol (0.4 g, 1.80 mmol) in DME (10 mL) was added t-BuOK (0.604 g, 5.4 mmol). The mixture was stirred for 30 min at rt, K2CO3 (0.621 g, 4.5 mmol) and 2-iodopropane (0.35 mL, 3.6 mmol) were added, and the reaction was heated at reflux for about 3 h. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine solution (10 mL), dried over Na2SO4 and concentrated under vacuum to obtain crude product. The crude product was purified by flash chromatography (silica gel, 60-120μ) using 10% ethyl acetate in hexane as eluent to afford 5-iodo-1-isopropylpyridin-2(1H)-one as an off-white solid (0.41 g, 67% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.90 (s, 1H), 7.49 (dd, 1H), 6.21 (d, 1H), 4.94 (t, 1H), 1.25 (t, 6H), LC-MS m/z calcd for [M+H]+ 263.98. found 264.0.

1. temperaturethe reaction was heated
2. temperatureat reflux for about 3 h
3. extractionextracted with ethyl acetate (2×100 mL)
4. washThe combined organic extracts were washed with brine solution (10 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under vacuum
7. customto obtain crude product
8. customThe crude product was purified by flash chromatography (silica gel, 60-120μ)

ORD record

ord-5ad7a70690c748e29e4d321d88b40280

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199975B2