Ethyl Acetate → HCID 90052275, compound

HRID 2284728Notes

Reaction equation

HRID 2284728 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[NH:7][C:6]=2[CH:19]=1.C(OCC)(=O)C.C(=O)([O-])O.[Na+].[CH3:31][Si:32]([C:35]#[CH:36])([CH3:34])[CH3:33]>O1CCCC1.C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:31][Si:32]([C:35]#[C:36][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[NH:7][C:6]=2[CH:19]=1)([CH3:34])[CH3:33]

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 516892Sodium BicarbonateHCID 90052266HCID 90052266, compound

Product 1

HCID 90052275HCID 90052275, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of tert-butyl ((6-iodo-1H-benzo[d]imidazol-2-yl)methyl)carbamate (G4, 216 mg), bis(triphenylphosphine)palladium(II) dichloride (40 mg) and copper(I) iodide (22 mg) in tetrahydrofuran (2 mL), triethylamine (243 μL) and trimethylsilylacetylene (96 μL) were added at room temperature, and the mixture was stirred at the same temperature for 3 hours. To the reaction mixture, ethyl acetate and saturated aqueous sodium hydrogencarbonate were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 70 to 0% hexane in ethyl acetate) to obtain tert-butyl ((6-((trimethylsilyl)ethynyl)-1H-benzo[d]imidazol-2-yl)methyl)carbamate (G5, 82 mg).

Workup

  1. additionwere added at room temperature
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluent, 70 to 0% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-9d7be923c7bd47a0a83828eb95a50b61
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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