m-Chloroperbenzoic acid → 3-bromo-2-methylthieno[2,3-c]pyridine-N-Oxide

HRID 2092325Notes

Reaction equation

HRID 2092325 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[S:4][C:3]=1[CH3:11].ClC1C=CC=C(C(OO)=[O:20])C=1>C(Cl)Cl.[OH-].[Na+]>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][N+:7]([O-:20])=[CH:8][CH:9]=2)[S:4][C:3]=1[CH3:11]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 584664443-Bromo-2-methylthieno[2,3-c]pyridine

Product 1

HCID 673397463-bromo-2-methylthieno[2,3-c]pyridine-N-Oxide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

3-Bromo-2-methylthieno[2,3-c]pyridine (0.500 g, 2.19 mmol) was dissolved in DCM (10 ml) and cooled down to 0° C. m-Chloroperbenzoic acid (0.737 g, 3.29 mmol) was added to the reaction portionwise while stirring. After 4 hours, the reaction wad diluted with 1N NaOH (10 ml) and DCM (10 ml). The layers were separated and the organic layer was washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate, reduced in vacuo and dried to give the title compound as a yellow solid. MS (M+H)+ 245

Workup

  1. additionwas added to the reaction portionwise
  2. customThe layers were separated
  3. washthe organic layer was washed (2×) with an aqueous saturated solution of sodium bicarbonate
  4. dry with materialThe organic layer was then dried with sodium sulfate
  5. customdried

Sources & evidence

ORD record
ord-ce5c6049da194d49bb947c569f859735
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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