Iodopentafluoroethane → HCID 49853555, Verbindung

To a solution of 2-aminopyridine (25.0 g, 263 mmol) in a mixture of water (250 ml) and tert-butyl methyl ether (25 ml) was added, successively perfluoroethyl iodide (80 g, 38 ml, 315 mmol), sodium hydrosulfite (64.6 g, 26 ml, 315 mmol), sodium hydrogen carbonate (26.5 g, 315.6 mmol) and tetrabutyl ammonium hydrogen sulfate (“TBAHS”) (0.11 equiv., 9.92 g, 28.9 mmol). The reaction mixture was stirred at ambient temperature for 16 h. The mixture was filtered and the filtrate was extracted twice with tert-butyl methyl ether. The combined organic phases were washed successively with water, aqueous hydrochloric acid (1N) and brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (AcOEt/cyclohexane) to give 5-(1,1,2,2,2-pentafluoroethyl)pyridin-2-amine in 7% yield. 1H NMR (400 MHz, CDCl3) 8.23 (d, 1H), 7.61 (d, 1H), 6.72 (m, 1H), 5.04 (sb, 2H, NH2) ppm. The major by-product was 3,5-bis(1,1,2,2,2-pentafluoroethyl)pyridin-2-amine.

1. additionwas added
2. filtrationThe mixture was filtered
3. extractionthe filtrate was extracted twice with tert-butyl methyl ether
4. washThe combined organic phases were washed successively with water, aqueous hydrochloric acid (1N) and brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated
7. customThe residue was purified by flash chromatography (AcOEt/cyclohexane)

ORD-Eintrag

ord-de29af16b93140d58208adafbb6ed116

Quelldatensatz

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09345244B2