Hydrogen Bromide → HCID 58046377, Verbindung

Temperatur

60 °C

1-(Imidazo[1,2-b]pyridazin-3-yl)ethanone (502 mg, 3.11 mmol) was dissolved in acetic acid (7.8 mL) and 33% HBr in acetic acid (0.564 mL, 3.11 mmol) was added. Bromine (0.177 mL, 3.43 mmol) was added and the solution stirred at 60° C. for 1.5 h. After stirring for 1.5 h, added more bromine (0.08 mL, 1.56 mmol) and 33% HBr in acetic acid (0.282 mL, 1.56 mmol). The solution was stirred at 60° C. for 3 h. The solution was then cooled to room temperature and quenched with 10% aqueous sodium thiosulfate. The aqueous layer was extracted with dichloromethane (×3). The organic layers were combined and washed with aqueous saturated sodium bicarbonate. The organic layer was collected and dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was taken on to the next step without further purification. 1H NMR (500 MHz, CD3SOCD3) δ 8.88 (d, 1H); 8.83 (s, 1H); 8.40 (d, 1H); 7.66 (s, 1H); 7.61 (dd, 1H). LRMS (APCI) calc'd for (C8H5Br2N3O) [M+H]+, 317.9. found 317.9.

1. stirringAfter stirring for 1.5 h
2. stirringThe solution was stirred at 60° C. for 3 h
3. temperatureThe solution was then cooled to room temperature
4. customquenched with 10% aqueous sodium thiosulfate
5. extractionThe aqueous layer was extracted with dichloromethane (×3)
6. washwashed with aqueous saturated sodium bicarbonate
7. customThe organic layer was collected
8. dry with materialdried with magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe residue was taken on to the next step without further purification

ORD-Eintrag

ord-799c2b2708b940ef9f7e5cb5df7aaa49

Quelldatensatz

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08592425B2