Dichloromethane → 5-Bromo-2-methanesulfinyl-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1, 2,4]triazine

HRID 1261891Notes

Reaction equation

HRID 1261891 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([S:11][CH3:12])=[N:6]2.C(Cl)Cl.C1C=C(Cl)C=C(C(OO)=[O:34])C=1>>[Br:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:14]=[CH:15][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:17][CH:18]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([S:11]([CH3:12])=[O:34])=[N:6]2

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 667117075-Bromo-7-(4-methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 667113545-Bromo-2-methanesulfinyl-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1, 2,4]triazineYield 96.3%

Procedure

Into a 30 mL vial, 5-Bromo-7-(4-methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (0.140 g, 0.000351 mol) and Methylene chloride (4 mL, 0.07 mol). m-CPBA 70-75% (70:30, m-Chloroperbenzoic acid:3-Chlorobenzoic acid, 0.0910 g, 0.000369 mol) was added portion wise over 10 minutes. The reaction was stirred at room temperature for 2 hours. HPLC suggested no starting material. The reaction was partitioned with DCM and NaHCO3. The organic was separated, washed with water, subsequently Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The organic was removed under vacuum to give 5-Bromo-2-methanesulfinyl-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazine as a yellow solid (140 mg, 96%). The solid was used as is without further purification.

Workup

  1. customThe reaction was partitioned with DCM and NaHCO3
  2. customThe organic was separated
  3. washwashed with water, subsequently Brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe solid was filtered
  6. washwashed with DCM
  7. customThe organic was removed under vacuum

Sources & evidence

ORD record
ord-46a7e981f26c40ed839fdeeaac580626
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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