Methyl iodide → 8-Methoxy-11-methyl-6,11-dihydro-5-thia-4,11-diaza-benzo[a]fluorene

HRID 2040486Notes

Reaction equation

HRID 2040486 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]1[C:12]3[CH:18]=[CH:19][CH:20]=[N:21][C:11]=3[S:10][CH2:9][C:8]2=1.[CH3:22]I>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:22])[C:13]1[C:12]3[CH:18]=[CH:19][CH:20]=[N:21][C:11]=3[S:10][CH2:9][C:8]2=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10778313HCID 10778313, compound

Product 1

HCID 596760788-Methoxy-11-methyl-6,11-dihydro-5-thia-4,11-diaza-benzo[a]fluorene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60%, 41 mg, 1.03 mmoL) was added into 8-methoxy-6,11-dihydro-5-thia-4,11-diaza-benzo[a]fluorene (250 mg, 0.933 mmoL) in DMF (3 mL) at 0° C. After 10 minutes, MeI (0.064 mL, 0.93 mmoL) was added dropwise into the reaction at 0° C. The reaction mixture was slowly warmed to room temperature over 2 hours. The reaction mixture was then partitioned between EtOAc and saturated NH4Cl. The aqueous phase was extracted two times with EtOAc. The organic layer from each extraction was combined, washed with 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, hexanes:EtOAc 1:1 as eluent) to yield the title compound as a white solid.

Workup

  1. customThe reaction mixture was then partitioned between EtOAc and saturated NH4Cl
  2. extractionThe aqueous phase was extracted two times with EtOAc
  3. extractionThe organic layer from each extraction
  4. washwashed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a brown oil
  9. customThe crude material (the oil) was then purified by column chromatography (silica gel, hexanes:EtOAc 1:1 as eluent)

Sources & evidence

ORD record
ord-cdbf9c3c7a8f45ac925bdca1a6338f45
Source dataset
uspto-grants-2013_11
Patent number
US08580840B2

Reaction notes

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