Ammonium Chloride → HCID 86707390, compound

Temperature

-20 °C

To a solution of 2,5-dichloro-3-nitropyridine (5.00 g, 25.9 mmol) in tetrahydrofuran (164 ml) was added a solution of 1 mol/L vinylmagnesium bromide in tetrahydrofuran (82.9 ml, 82.9 mmol) at −78° C. The mixture was stirred at −20° C. overnight, and then to the reaction solution was added saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate twice. The organic layer was combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→7:3), and then washed with diisopropyl ether to give 4,7-dichloro-1H-pyrrolo[2,3-c]pyridine (1.12 g, 23%) as a pale yellow powder.

1. extractionThe mixture was extracted with ethyl acetate twice
2. washwashed with water and saturated brine
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationconcentrated under reduced pressure
5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→7:3)
6. washwashed with diisopropyl ether

ORD record

ord-65facd3fcc574dfdb37cca4373b21559

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987445B2