Hydrogen Peroxide → 2-Methanesulfonyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine

HRID 1262399Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]2[C:12]([CH:13]=[N:14][C:15](SC)=[N:16]2)=[CH:11][CH:10]=1.OO.[O-:22][S:23]([O-:26])(=S)=O.[Na+].[Na+].[CH3:29]O>O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH3:29][S:23]([C:15]1[N:14]=[CH:13][C:12]2=[CH:11][CH:10]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[N:17]2[N:16]=1)(=[O:26])=[O:22]

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium Tungstate Dihydrate (62 mg, 0.19 mmol) and 7-(2-Methoxy-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (1.02 g, 3.76 mmol) were combined in Methanol (40.0 mL) and 50% Hydrogen Peroxide (0.65 mL, 11 mmol) was added and the reaction was stirred under an atmosphere of nitrogen at 60° C. for 5 h. The mixture was treated with 5 mL 10% Na2S2O3, generating a ppt, then allowed to cool to rt before being stored in a freezer for 30 min. The resultant solids were collected on a Buchner, washing with water (25 mL). Further drying in vacuo afforded 2-Methanesulfonyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (1.00 g; Yield=87.7%). 1H-NMR (DMSO-d6): 9.38 (s, 1H), 7.75 (dd, 1H, J=1.6, 7.6 Hz), 7.51 (m, 2H), 7.40 (d, 1H, J=4.7 Hz), 7.25 (d, 1H, J=8.3 Hz), 7.13 (m, 1H), 3.83 (s, 3H), 3.37 (s, 3H).

Workup

temperatureto cool to rt
waitbefore being stored in a freezer for 30 min
customThe resultant solids were collected on a Buchner
washwashing with water (25 mL)
customFurther drying in vacuo

Sources & evidence

ORD record: ord-cb4349d6b4f3416f8a43ace5cb98ec7b
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

Loading…