Acetic Acid → 7-Bromo-3-methyl-(1,2,4)triazolo(4,3-a)pyridine

HRID 879569Notes

Reaction equation

HRID 879569 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][NH2:9])[CH:3]=1.[C:10](O)(=O)[CH3:11]>>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:10]([CH3:11])=[N:9][N:8]=[C:4]2[CH:3]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 534028634-Bromo-2-hydrazinylpyridine

Product 1

HCID 468399207-Bromo-3-methyl-(1,2,4)triazolo(4,3-a)pyridine

Conditions

Temperature
125 °C

Procedure

To a vial flushed with argon was added 4-bromo-2-hydrazinylpyridine (1.88 g, 10 mmol) and acetic acid (2.5 mL). The mixture was refluxed at 125° C. under argon for 16 hours. After cooling to room temperature, acetic acid was distilled off, and to the residue was added saturated NaHCO3 (150 mL) and DCM (150 mL). The aqueous layer was extracted with DCM, the organic extracts were combined, dried over MgSO4, and concentrated to give the product. 1H NMR (400 MHz, CDCl3) δ 7.95-7.90 (m, 1H), 7.73 (d, J=7.3 Hz, 1H), 6.94 (dd, J=7.3, 1.7 Hz, 1H), 2.74 (s, 3H).

Workup

  1. customTo a vial flushed with argon
  2. temperatureAfter cooling to room temperature
  3. distillationacetic acid was distilled off
  4. additionto the residue was added saturated NaHCO3 (150 mL) and DCM (150 mL)
  5. extractionThe aqueous layer was extracted with DCM
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customto give the product

Sources & evidence

ORD record
ord-da89150a69394045afcb8449de1cc9c6
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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