Methyl iodide → HCID 66834850, compound

HRID 2275219Notes

Reaction equation

HRID 2275219 reaction equation
[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7](=[O:30])[C:8]4[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@H:23]5[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24]5)=[CH:17][C:9]=4[C:10]([CH3:16])([CH3:15])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:33]I.[Cl-].[NH4+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7](=[O:30])[C:8]4[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@H:23]5[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24]5)=[CH:17][C:9]=4[C:10]([CH3:15])([CH3:16])[C:11]=3[N:12]2[CH3:33])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 24477Sodium ThiosulfateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 668346753-bromo-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one

Product 1

HCID 66834850HCID 66834850, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under nitrogen atmosphere, to the DMF (1 mL) suspension of 3-bromo-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound T18-1, 112.2 mg, 0.239 mmol) and sodium hydride (60%) (19 mg, 0.477 mmol), cooled in an ice bath, methyl iodide (37 mL, 0.596 mmol) was added. The reaction mixture was stirred at room temperature for 45 min, and then added with saturated aqueous solution of ammonium chloride and saturated aqueous solution of sodium thiosulfate under ice cooling. The mixture was extracted twice with ethyl acetate/diethyl ether/hexane. The organic layer was washed with water and subsequently with aqueous solution of ammonium chloride, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting crude product was purified by flash column chromatography {Merck Kieselgel60, solution for elution:hexane/ethyl acetate (1:1)} to obtain the title compound (white solid, 107.3 mg, 93%).

Workup

  1. temperaturecooled in an ice bath
  2. extractionThe mixture was extracted twice with ethyl acetate/diethyl ether/hexane
  3. washThe organic layer was washed with water and subsequently with aqueous solution of ammonium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude product was purified by flash column chromatography {Merck Kieselgel60, solution for elution

Sources & evidence

ORD record
ord-6af35cc52973487e949fcd02d212f971
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Reaction notes

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