Methyl iodide → HCID 59676093, compound

HRID 2357155Notes

Reaction equation

HRID 2357155 reaction equation
[CH3:1]I.[CH3:3][O:4][C:5]1[CH:23]=[CH:22][C:8]2[C:9]3[NH:10][C:11]4[C:16]([C:17]=3[CH2:18][S:19][C:7]=2[CH:6]=1)=[CH:15][C:14]([O:20][CH3:21])=[CH:13][CH:12]=4.[H-].[Na+]>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:23]=[CH:22][C:8]2[C:9]3[N:10]([CH3:1])[C:11]4[C:16]([C:17]=3[CH2:18][S:19][C:7]=2[CH:6]=1)=[CH:15][C:14]([O:20][CH3:21])=[CH:13][CH:12]=4

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59676057HCID 59676057, compound

Product 1

HCID 59676093HCID 59676093, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

CH3I (108 mg, 0.758 mmol, 1.5 eq.) was added to a mixture of 3,8-dimethoxy-6,11-dihydro-5-thia-11-aza-benzo[a]fluorene (150 mg, 0.505 mmol) and NaH (61 mg, 60% in mineral oil, 1.515 mmol, 3.0 eq.) in DMF. The reaction mixture was then stirred at 25° C. for 2 hours. The reaction mixture was partitioned between EtOAc and saturated NaHCO3 aqueous solution. The aqueous layer was extracted three times with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a crude material. The crude material was purified by silica gel (Hexanes to EtOAc 4:1) to yield the title compound as a brown solid.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and saturated NaHCO3 aqueous solution
  2. extractionThe aqueous layer was extracted three times with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a crude material
  8. customThe crude material was purified by silica gel (Hexanes to EtOAc 4:1)

Sources & evidence

ORD record
ord-d8a6996820f6445eb4506eb0e4a1f16c
Source dataset
uspto-grants-2010_07
Patent number
US07759498B2

Reaction notes

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