Iodopentafluoroethane → HCID 49853555、化合物

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レコード

ord-de29af16b93140d58208adafbb6ed116

出典データセット

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09345244B2