Stannous Chloride → HCID 22240103, compound

HRID 891863Notes

Reaction equation

HRID 891863 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[N:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][C:3]=1[N+:21]([O-])=O.[Sn](Cl)Cl>CCO.O1CCOCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[N:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][C:3]=1[NH2:21]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 22240094HCID 22240094, compound

Product 1

HCID 22240103HCID 22240103, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 22560076Dioxan ethanolSolvent

Conditions

Temperature
50 °C

Procedure

7-(4-Methyl-3-nitrophenyl)-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.27 g, 0.83 mmol) was dissolved in EtOH/1,4-dioxane (20 ml, 1:1) at ambient temperature under an atmosphere of nitrogen and tin(II) chloride (0.80 g, 4.13 mmol) added. This stirred mixture was warmed at 50° C. for 6 h. The solvents were removed in vacuo, ice-water/NaHCO3 was added and extracted with dichloromethane. These extracts were washed with water and saturated brine then dried (MgSO4), filtered and concentrated in vacuo. Purification by chromatography (silica gel, dichloromethane) gave 0.24 g of the title compound as a red solid: 1H NMR (400 MHz, CDCl3) δ 2.26 (3H, s), 3.75–3.85 (2H, br), 7.22 (1H, d, J 7.8), 7.40 (1H, dd, J 1.7, 7.8), 7.43 (1H, d, J 1.7), 8.55 (1H, s), 8.76 (1H, s); MS (ES+) m/z 294 [M+H]+.

Workup

  1. customThe solvents were removed in vacuo, ice-water/NaHCO3
  2. additionwas added
  3. extractionextracted with dichloromethane
  4. washThese extracts were washed with water and saturated brine
  5. dry with materialthen dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by chromatography (silica gel, dichloromethane)

Sources & evidence

ORD record
ord-7f819dc655634f66a52f61aee0f62e71
Source dataset
uspto-grants-2006_02
Patent number
US07005431B2

Reaction notes

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