Hydrogen Peroxide → 7-(2,2-Difluoro-benzo[1,3]dioxol-4-yl)-2-methanesulfonyl-pyrrolo[2,1-f][1,2,4]triazine

HRID 1262422Notes

Reaction equation

[F:1][C:2]1([F:22])[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]3[N:19]4[C:14]([CH:15]=[N:16][C:17](SC)=[N:18]4)=[CH:13][CH:12]=3)[C:4]=2[O:3]1.OO.[S:25]([O-:29])([O-])(=[O:27])=S.[Na+].[Na+].[CH3:32]O>O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[F:22][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]3[N:19]4[C:14]([CH:15]=[N:16][C:17]([S:25]([CH3:32])(=[O:29])=[O:27])=[N:18]4)=[CH:13][CH:12]=3)[C:4]=2[O:3]1

Participants

Conditions

Temperature: 55 °C

Procedure

7-(2,2-Difluoro-benzo[1,3]dioxol-4-yl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (0.435 g, 1.35 mmol) and Sodium Tungstate Dihydrate (59 mg, 0.18 mmol) were suspended in Methanol (15.0 mL), then 50% Hydrogen Peroxide (0.350 mL, 6.16 mmol) was added. The mixture was then heated at 55° C. overnight. A solution of sodium thiosulfate was added, stirred 10 min, then cooled to rt. The product was collected by filtration, washing the yellow solids with 1:1 MeOH:H2O (10 mL). After drying on the Buchner funnel, 7-(2,2-Difluoro-benzo[1,3]dioxol-4-yl)-2-methanesulfonyl-pyrrolo[2,1-f][1,2,4]triazine (0.410 g; Yield=85.7%). LCMS (HPLC): 1.15 min, m/z=354 (M+H); 1H-NMR (DMSO-d6): 9.51 (s, 1H), 8.16 (d, 1H, J=8.1 Hz), 7.73 (d, 1H, J=4.8 Hz), 7.56 (d, 1H, J=7.7 Hz), 7.49 (d, 1H, J=4.8 Hz), 7.45 (m, 1H), 3.45 (s, 3H).

Workup

temperaturecooled to rt
filtrationThe product was collected by filtration
washwashing the yellow solids with 1:1 MeOH

Sources & evidence

ORD record: ord-fa82831066ed4f539dc104d53c460898
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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