Hydrogen Bromide → 1-(6-Methylpyridin-2-yl)-2-([1,2,4]triazolo[1,5-a]pyridin-6-yl)ethane-1,2-dione

Temperature

65 °C

To a stirred suspension of 2-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1-(6-methylpyridin-2-yl)ethanone (6.20 g, 24.57 mmol) in DMSO (48 mL) was added dropwise HBr (48 wt. % in water, 5.96 g, 12.4 mL) at 0° C., and the mixture was heated at 60-70° C. After 2 h, the reaction mixture was cooled to 0° C., poured onto ice water (20 mL), and basified to pH 10 with solid K2CO3. The mixture was extracted with CHCl3 (2×250 mL), and the organic phase was washed with water (2×100 mL), dried over anhydrous Na2SO4, filtered, and evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel using a mixture of MeOH and CH2Cl2 as eluent to give the titled compound (6.02 g, 92%) as a light yellow solid. 1H NMR (400 MHz, CDCl3): δ 9.11 (dd, 1H, J=1.6, 1.2 Hz), 8.47 (s, 1H), 8.14 (dd, 1H, J=9.2, 1.6 Hz), 8.04 (br d, 1H, J=7.6 Hz), 7.88 (dd, 1H, J=9.2, 1.2 Hz), 7.84 (t, 1H, J=7.8 Hz), 7.42 (br d, 1H, J=8.0 Hz), 2.49 (s, 3H).

1. temperaturethe reaction mixture was cooled to 0° C.
2. additionpoured onto ice water (20 mL)
3. extractionThe mixture was extracted with CHCl3 (2×250 mL)
4. washthe organic phase was washed with water (2×100 mL)
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. customevaporated to dryness under reduced pressure
8. customThe residue was purified by MPLC on silica gel using
9. additiona mixture of MeOH and CH2Cl2 as eluent

ORD record

ord-eaa64032ed854843a14528d3e83f43f7

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080568B1