Dichloromethane → 2-(Methylsulfinyl)-7-(4-(methylsulfonyl)phenyl)pyrrolo[2,1-f][1,2,4]triazine

HRID 1261883Notes

Reaction equation

HRID 1261883 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:19]3[C:14]([CH:15]=[N:16][C:17]([S:20][CH3:21])=[N:18]3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(Cl)Cl.ClC1C=CC=C(C(OO)=[O:33])C=1.C([O-])(O)=O.[Na+]>>[CH3:21][S:20]([C:17]1[N:16]=[CH:15][C:14]2=[CH:13][CH:12]=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=3)[N:19]2[N:18]=1)=[O:33]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 667120257-(4-Methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 667110462-(Methylsulfinyl)-7-(4-(methylsulfonyl)phenyl)pyrrolo[2,1-f][1,2,4]triazine

Procedure

Into a Round bottom flask, 7-(4-Methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (0.630 g, 0.00197 mol) and Methylene chloride (50 mL, 0.8 mol) were added. m-Chloroperbenzoic acid (0.464 g, 0.00207 mol) was added portion wise. The reaction was stirred at room temperature for 30 minutes. Saturated NaHCO3 was added. The organic layer was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The organic was removed under vacuum. to give 2-Methanesulfinyl-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazine a yellow solid (0.63 g, 93%). NMR 1H (DSMO-d6)-9.40 (s, 1H), 8.54 (d, 2H, J=8.60 Hz), 8.09 (d, 2H, J=7.56 Hz), 7.85 (d, 1H, J=4.84 Hz), 7.39 (d, 1H, J=4.88 Hz), 3.29 (s, 3H), 3.00 (s, 3H)

Workup

  1. customThe organic layer was separated
  2. washwashed with Brine
  3. dry with materialdried over Na2SO4
  4. filtrationThe solid was filtered
  5. washwashed with DCM
  6. customThe organic was removed under vacuum

Sources & evidence

ORD record
ord-bb04eaa5fb3543a7a47e2d8ef08bda7d
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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