Water → HCID 59424456, compound

HRID 1711007Notes

Reaction equation

HRID 1711007 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([S:14][CH3:15])[S:13][C:6]=12.C1C=C(Cl)C=C(C(OO)=[O:31])C=1.O>C(Cl)Cl>[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([S:14]([CH3:15])=[O:31])[S:13][C:6]=12

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 594244887-(2-Fluoro-4-nitrophenoxy)-2-(methylthio)thieno[3,2-b]pyridine

Product 1

HCID 59424456HCID 59424456, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 230 (400 mg, 1.189 mmol, scheme 50) in DCM (12 mL) at 0° C. was added m-CPBA (77%, 272 mg, 1.189 mmol). The reaction mixture was stirred at 0° C. for 30 minutes, water was added and the phases were separated. The organic phase was collected, washed with a 1% sodium hydroxide solution, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography, eluent DCM/MeOH (20:1), to afford title compound 233 (414 mg, 90% yield, crude), which was used in the next step without further purification. MS (m/z): 353.0 (M+1).

Workup

  1. customthe phases were separated
  2. customThe organic phase was collected
  3. washwashed with a 1% sodium hydroxide solution
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography, eluent DCM/MeOH (20:1)

Sources & evidence

ORD record
ord-3c7968555cb94fc88e5db1418e747004
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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