Imidazole → HCID 157380137, compound

HRID 227431Notes

Reaction equation

HRID 227431 reaction equation
[N:1]1(CO)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.N1[CH:16]=[CH:15]N=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])(C)C.[OH2:25].Cl[CH2:27]Cl>>[C:20]([SiH2:17][O:25][C:15]([CH3:16])([CH3:27])[C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]2)([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 5

HCID 795ImidazoleHCID 962WaterHCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 12568141HCID 12568141, compound

Product 1

HCID 157380137HCID 157380137, compoundYield 91%

Procedure

To a solution of indole-1-methanol (Combi-Blocks, 1.0 g, 6.8 mmol) in 50 mL of dichloromethane was added imidazole (0.56 g, 8.2 mmol) followed by tert-butyldimethylsilyl chloride (1.1 g, 7.0 mmol). The mixture was stirred at ambient temperature for 17 hours then 10 mL H2O was added and the layers were separated. The aqueous layer was extracted 3×5 mL of dichloromethane and the combined organic extracts were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via flash column chromatography (SiO2, 80% hexanes in EtOAc) to provide the title compound (1.6 g, 6.2 mmol, 91% yield). MS (DCI/NH3) m/z 262 (M+H)+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted 3×5 mL of dichloromethane
  3. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. custompurified via flash column chromatography (SiO2, 80% hexanes in EtOAc)

Sources & evidence

ORD record
ord-a6e5c87093024269add575d70edb256f
Source dataset
uspto-grants-2009_07
Patent number
US07560481B2

Reaction notes

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