Sodium periodate → 3-Benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazine-2-carbaldehyde

HRID 1795976Notes

Reaction equation

HRID 1795976 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH2:7]([N:14]1[C:19](=[O:20])[C:18]2=[C:21]([Cl:24])[CH:22]=[CH:23][N:17]2[N:16]=[C:15]1[CH:25]=CN(C)C)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([N:14]1[C:19](=[O:20])[C:18]2=[C:21]([Cl:24])[CH:22]=[CH:23][N:17]2[N:16]=[C:15]1[CH:25]=[O:2])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 867599833-Benzyl-5-chloro-2-(2-dimethylamino-vinyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one

Product 1

HCID 221800693-Benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazine-2-carbaldehydeYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium periodate (17.3 g, 80.7 mmol) was added to a pH 7.0 buffered solution (75 mL) of 3-benzyl-5-chloro-2-(2-dimethylamino-vinyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (5.3 g, 16.1 mmol) in THF (150 mL) at room temperature. The reaction mixture was stirred at room temperature for 1.5 h. The reaction mixture was filtered through Celite® and the solids washed with CHCl3 (100 ml). The filtrate was wash with saturated NaCl (2×50 mL), dried (Na2SO4), filtered and concentrated in vacuo. The solid was azeotroped with toluene (2×50 mL) to afford the title compound as a solid (4.6 g, 100%): TLC, Rf=0.5 (2/1 hexane/EtOAc, UV); 1H NMR (CDCl3) δ 9.34 (s, 1H), 7.33 (m, 1H), 7.16–7.27 (m, 5H), 6.60 (m, 1H), 5.62 (s, 2H).

Workup

  1. customat room temperature
  2. filtrationThe reaction mixture was filtered through Celite®
  3. washthe solids washed with CHCl3 (100 ml)
  4. washThe filtrate was wash with saturated NaCl (2×50 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe solid was azeotroped with toluene (2×50 mL)

Sources & evidence

ORD record
ord-fd8472dc6ae144e39735ee894791471a
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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