Acetic Acid → 2-Methanesulfonyl-7-pyridin-2-yl-pyrrolo[2,1-f][1,2,4]triazine

HRID 1262443Notes

Reaction equation

CS[C:3]1[N:8]=[CH:7][C:6]2=[CH:9][CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[N:5]2[N:4]=1.[C:18](O)(=O)C.OO.[O-:24][S:25]([O-:28])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>CO.O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH3:18][S:25]([C:3]1[N:8]=[CH:7][C:6]2=[CH:9][CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[N:5]2[N:4]=1)(=[O:28])=[O:24]

Participants

Conditions

Temperature: 65 °C

Procedure

2-Methylsulfanyl-7-pyridin-2-yl-pyrrolo[2,1-f][1,2,4]triazine (0.173 g, 0.714 mmol) was dissolved in Methanol (5.00 mL) and Sodium Tungstate Dihydrate (19.0 mg, 0.0576 mmol), Acetic acid (0.338 mL, 5.94 mmol) and 50% Hydrogen Peroxide (0.150 mL, 2.64 mmol) were added. The reaction mixture was then stirred and heated at 65° C. overnight. More 50% Hydrogen Peroxide (0.1 mL) was added and the reaction continued stirring. Once the reaction was complete, 5 mL of 10% Na2S2O3 and 2 mL 50% sat. NaHCO3 were added and the reaction was let cool to room temperature followed by refrigeration. The precipitate was then filtered and placed on the high vac to afford 2-Methanesulfonyl-7-pyridin-2-yl-pyrrolo[2,1-f][1,2,4]triazine.

Workup

stirringthe reaction continued stirring
temperaturethe reaction was let cool to room temperature
filtrationThe precipitate was then filtered

Sources & evidence

ORD record: ord-33e45b9fcec84a45a97476a48254b870
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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