m-Chloroperbenzoic acid → HCID 9967967, compound

HRID 1633788Notes

Reaction equation

HRID 1633788 reaction equation
[F:1][C:2]1[C:3]2[C:4]3[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]=3[C:12]([C:19]1[NH:20][CH:21]=[CH:22][CH:23]=1)=[CH:13][C:14]=2[S:15][CH2:16][CH2:17][OH:18].C1C=C(Cl)C=C(C(OO)=[O:32])C=1>C1COCC1.C(OCC)(=O)C>[F:1][C:2]1[C:3]2[C:4]3[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]=3[C:12]([C:19]1[NH:20][CH:21]=[CH:22][CH:23]=1)=[CH:13][C:14]=2[S:15]([CH2:16][CH2:17][OH:18])=[O:32]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 9967203HCID 9967203, compound

Product 1

HCID 9967967HCID 9967967, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-fluoro-5-(2-hydroxy-ethylsulfanyl)-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one (from Example 36 above) (15 mg, 0.05 mmol) in THF (approximately 7 mL) was treated with mCPBA (Acros, 14 mg, 0.06 mmol, 75%). After 20 minutes, the reaction mixture was diluted with ethyl acetate and washed with aqueous saturated Na2S2O3 and aqueous saturated NaHCO3. The organic layer was dried over Na2SO4 and concentrated. The resulting residue was purified by flash chromatography (silica gel, 0-100% ethyl acetate in hexanes gradient), followed by precipitation out of THF with excess pentane to give 6-fluoro-5-(2-hydroxy-ethanesulfinyl)-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one as a yellow solid. (Yield 15 mg, 96%).

Workup

  1. washwashed with aqueous saturated Na2S2O3 and aqueous saturated NaHCO3
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by flash chromatography (silica gel, 0-100% ethyl acetate in hexanes gradient)
  5. customfollowed by precipitation out of THF with excess pentane

Sources & evidence

ORD record
ord-854fdf2a8c3141b887e8b3c498a6c327
Source dataset
uspto-grants-2003_01
Patent number
US06504034B2

Reaction notes

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