Oxygen → HCID 59676064, compound

HRID 642783Notes

Reaction equation

HRID 642783 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[C:10]3[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=3[S:8][CH2:7][C:6]2=1.[O:20](C(C)(C)C)[K].O=O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[C:10]3[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=3[S:8](=[O:20])[CH2:7][C:6]2=1

Participants

5

Reactant 3

HCID 977OxygenHCID 2891388-Methoxy-6,11-dihydrothiochromeno[4,3-b]indoleHCID 178418922HCID 178418922, compound

Product 1

HCID 59676064HCID 59676064, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Methoxy-6,11-dihydro-5-thia-11-aza-benzo[a]fluorene (79 mg, 0.281 mmoL) in DMF (5 mL) was treated with KO-t-Bu (1.0 M in THF, 0.48 mL, 0.48 mmoL) under a flow of O2 for 6 hours. The reaction mixture was then partitioned between water and EtOAc. The EtOAc layer was washed with saturated NH4Cl, water, brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a brown oil. The crude material (the oil) was then purified by column chromatography (silica gel, CH2Cl2: MeOH 9:1 as eluent) to yield the title compound as a white solid.

Workup

  1. customThe reaction mixture was then partitioned between water and EtOAc
  2. washThe EtOAc layer was washed with saturated NH4Cl, water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a brown oil
  7. customThe crude material (the oil) was then purified by column chromatography (silica gel, CH2Cl2: MeOH 9:1 as eluent)

Sources & evidence

ORD record
ord-5f76ea01cc384e2ca5b6e4a3dd8c7787
Source dataset
uspto-grants-2010_04
Patent number
US07696239B2

Reaction notes

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