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

HRID 659151Notes

Reaction equation

HRID 659151 reaction equation
[N:1]1[CH:2]=[N:3][N:4]2[CH:9]=[C:8]([CH2:10][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=3)=[O:12])[CH:7]=[CH:6][C:5]=12.Br.C([O-])([O-])=[O:22].[K+].[K+]>CS(C)=O>[N:1]1[CH:2]=[N:3][N:4]2[CH:9]=[C:8]([C:10](=[O:22])[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=3)=[O:12])[CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 666325661-(6-Methylpyridin-2-yl)-2-([1,2,4]triazolo[1,5-a]pyridin-6-yl)ethan-1-one

Product 1

HCID 510516441-(6-Methylpyridin-2-yl)-2-([1,2,4]triazolo[1,5-a]pyridin-6-yl)ethane-1,2-dioneYield 92%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-eaa64032ed854843a14528d3e83f43f7
Source dataset
uspto-grants-2011_12
Patent number
US08080568B1

Reaction notes

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