Iodine → HCID 86704621, Verbindung

Temperatur

80 °C

A mixture of the title compound from Step A (2.1 g, 3.75 mmol), n-pentyl nitrite (0.66 g, 5.62 mmol) and I2 (1.24 g, 4.87 mmol) in chloroform (20 mL) was stirred at 80° C. for 1 h. The mixture was cooled, and the solvent was diluted with CH2Cl2. The mixture was washed with Na2S2O3 (5 mL), and with brine (5 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 40M, eluting with EtOAc/hexane (10/90) to give the title compound as a yellow gum. 1H NMR (CDCl3, 500 MHz) δ 8.41 (s, 1H), 7.92 (s, 1H), 7.78 (s, 2H), 7.77 (m, 1H), 7.35 (m, 1H), 7.22 (m, 1H), 5.76 (d, J=8.5 Hz, 1H), 4.91 (d, J=17 Hz, 1H), 4.45 (m, 1H), 4.06 (d, J=17.5 Hz, 1H), 2.64 (s, 3H), 0.76 (d, J=7 Hz, 3H). LCMS=672.1 (M+H)+.

1. temperatureThe mixture was cooled
2. washThe mixture was washed with Na2S2O3 (5 mL)
3. dry with materialwith brine (5 mL), dried (Na2SO4)
4. filtrationfiltered
5. customthe solvent was evaporated under reduced pressure
6. customThe residue was purified by column chromatography on silica gel Biotage 40M
7. washeluting with EtOAc/hexane (10/90)

ORD-Eintrag

ord-4124e88bc6ed4498a17fa3e80beefa65

Quelldatensatz

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09221834B2