m-Chloroperbenzoic acid → 7-Bromo-2-(methylsulfinyl)pyrrolo[2,1-f][1,2,4]triazine

HRID 1261936Notes

Reaction equation

HRID 1261936 reaction equation
[Br:1][C:2]1[N:10]2[C:5]([CH:6]=[N:7][C:8]([S:11][CH3:12])=[N:9]2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:21])C=1>C(Cl)Cl>[Br:1][C:2]1[N:10]2[C:5]([CH:6]=[N:7][C:8]([S:11]([CH3:12])=[O:21])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 574161287-Bromo-2-(methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 580713077-Bromo-2-(methylsulfinyl)pyrrolo[2,1-f][1,2,4]triazineYield 76.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a Round bottom flask, 7-Bromo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (4.00 g, 0.0164 mol) and Methylene chloride (100 mL) were added. m-Chloroperbenzoic acid (77% max)(5.14 g, 0.0229 mol) was added portion wise over 20 minutes and the reaction was stirred at room temperature for one hour. The mixture was partitioned with DCM (200 mL) and saturated NaHCO3 (200 mL). Organic extracts were washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum to give a yellow solid. The solid was washed with hexane to afford 3.27 grams of 7-Bromo-2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazine as a yellow powder. 1H NMR (400 MHz, DMSO, d6) δ 9.34 (s, 1H), 7.51 (m, 1H), 7.41 (d, 1H, J=4.71 Hz), 3.43 (s, 3H).

Workup

  1. customThe mixture was partitioned with DCM (200 mL) and saturated NaHCO3 (200 mL)
  2. washOrganic extracts were washed with Brine
  3. dry with materialdried over Na2SO4
  4. filtrationThe solid was filtered
  5. washwashed with DCM
  6. customThe solvent was removed under vacuum
  7. customto give a yellow solid
  8. washThe solid was washed with hexane

Sources & evidence

ORD record
ord-3cbe75ad90dd40689b057ff82079cc51
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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