Phosphorus oxychloride → HCID 59233259, compound

HRID 1925137Notes

Reaction equation

HRID 1925137 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:10](=O)[C:11]([C:14]2[N:15]=[N:16][C:17]([Cl:20])=[CH:18][CH:19]=2)([F:13])[F:12])=[N:6][CH:7]=1.P(Cl)(Cl)(Cl)(Cl)Cl.O=P(Cl)(Cl)Cl>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([C:11]([C:14]3[N:15]=[N:16][C:17]([Cl:20])=[CH:18][CH:19]=3)([F:13])[F:12])=[N:9][N:8]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 59233291N'-(5-bromopyridin-2-yl)-2-(6-chloropyridazin-3-yl)-2,2-difluoroacetohydrazide

Product 1

HCID 59233259HCID 59233259, compoundYield 84%

Conditions

Temperature
140 °C

Procedure

A mixture of N′-(5-bromopyridin-2-yl)-2-(6-chloropyridazin-3-yl)-2,2-difluoroacetohydrazide (1.0 g, 2.64 mmol) and PCl5 (1.2 g, 8 mmol) in POCl3 (40.5 g, 264 mmol) was heated at 140° C. in a sealed tube for 18 hrs. Solvent was removed via rotary evaporation, and the resulting residue was reconstituted in EtOAc. The organic solution was washed with saturated NaHCO3, dried with MgSO4, filtered, and concentrated to dryness. The resulting material was purified via MPLC (Hex:EtOAc, 50-100% gradient) to provide the title compound, 6-bromo-3-((6-chloropyridazin-3-yl)difluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine 45F (0.8 g, 2.21 mmol, 84%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.75 (dd, J=9.85, 1.77 Hz, 1 H) 8.01 (dd, J=9.85, 1.01 Hz, 1 H) 8.31 (d, J=9.09 Hz, 1 H) 8.42-8.51 (m, 1 H) 8.93 (s, 1 H). ESI-MS:m/z 359.9 (M+H)+.

Workup

  1. customSolvent was removed via rotary evaporation
  2. washThe organic solution was washed with saturated NaHCO3
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe resulting material was purified via MPLC (Hex:EtOAc, 50-100% gradient)

Sources & evidence

ORD record
ord-1b360e952c4746729feba85fba6764cc
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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