Sulfate Ion → HCID 59377444, compound

HRID 386658Notes

Reaction equation

HRID 386658 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[NH:7][CH:6]=[CH:5]2.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].Br[CH2:25][CH2:26][O:27][Si:28]([CH3:34])([CH3:33])[C:29]([CH3:32])([CH3:31])[CH3:30].S([O-])([O-])(=O)=O>CN(C=O)C.C1(C)C=CC=CC=1>[C:29]([Si:28]([CH3:34])([CH3:33])[O:27][CH2:26][CH2:25][N:7]1[C:8]2[C:4](=[CH:3][C:2]([CH3:1])=[C:10]([N+:11]([O-:13])=[O:12])[CH:9]=2)[CH:5]=[CH:6]1)([CH3:32])([CH3:31])[CH3:30]

Participants

7

Reactant 4

HCID 1117Sulfate IonHCID 2733832Lithium HexamethyldisilazideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 212183045-Methyl-6-nitro-1H-indole

Product 1

HCID 59377444HCID 59377444, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

To an ice cold solution of 352 mg of 5-methyl-6-nitroindole in 10 mL DMF was added drop wise 2.2 ml of 1M toluene solution of lithium hexamethyldisilazide. The solution was stirred for five minutes and 0.5 ml (1.1 equivalents) bromoethoxy dimethyl-t-butyl silane was added. The mixture was stirred at 0° C. for 30 minutes and then stirred for 4 hours at room temperature. Sulfate buffer (pH2) was added and the mixture was extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography to yield 300 mg of 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-6-nitro-1H-indole.

Workup

  1. stirringThe mixture was stirred at 0° C. for 30 minutes
  2. stirringstirred for 4 hours at room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-48397410699148c4b3239f1a4fd1ee19
Source dataset
uspto-grants-2013_02
Patent number
US08372865B2

Reaction notes

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