Citric Acid → HCID 58306784, compound

HRID 1909880Notes

Reaction equation

HRID 1909880 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[OH:13])[CH:8]=[CH:7]2.[C:20]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])([CH3:22])[CH3:21].N1C=CN=C1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH:12]([O:13][Si:24]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:26])[CH3:25])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 311Citric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 58306818HCID 58306818, compound

Product 1

HCID 58306784HCID 58306784, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-(7-bromo-1H-indol-1-yl)-1-phenylethanol (0.70 g) were added DMF (7.0 mL), tert-butyl(chloro)dimethylsilane (0.47 g), and imidazole (0.23 g), followed by stirring at room temperature for 25 hours. To the reaction mixture was added a 10% aqueous citric acid solution (15 mL), followed by extraction with ethyl acetate, and the obtained organic layer was washed with brine. After drying over anhydrous sodium sulfate and concentrating under reduced pressure, the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=99/1-90/10) to obtain 7-bromo-1-(2-{[tert-butyl(dimethyl)silyl]oxy}-2-phenylethyl)-1H-indole (0.92 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washthe obtained organic layer was washed with brine
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. concentrationconcentrating under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=99/1-90/10)

Sources & evidence

ORD record
ord-107b1691de5b451fb657570884ef056a
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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