Hydrochloric Acid → Methyl 2-(benzamido)-4-(2-(trimethylsilyl)ethynyl)benzoate

HRID 1673346Notes

Reaction equation

HRID 1673346 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C1(C)C=CC=CC=1.[C:14]([NH:22][C:23]1[CH:32]=[C:31](Br)[CH:30]=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C(OCC)(=O)C.C(N(CC)CC)C>[C:14]([NH:22][C:23]1[CH:32]=[C:31]([C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])[CH:30]=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 66111TrimethylsilylacetyleneHCID 57879335Methyl 2-(benzamido)-4-bromobenzoate

Product 1

HCID 57879451Methyl 2-(benzamido)-4-(2-(trimethylsilyl)ethynyl)benzoate

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

2.7 mL of (trimethylsilyl)acetylene was added to 30 mL of toluene suspension containing 3.2 g of methyl 2-(benzamido)-4-bromobenzoate, 92 mg of copper (I) iodide, 0.34 g of bis(triphenylphosphine)palladium (II) chloride and 2.7 mL of triethylamine at room temperature and stirred under nitrogen atmosphere at 70 to 80° C. for 2 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 1.0 mol/L hydrochloric acid were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 1.0 mol/L hydrochloric acid and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated, under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue and a solid substance was separated by filtration to obtain 3.5 g of methyl 2-(benzamido)-4-(2-(trimethylsilyl)ethynyl)benzoate as pale yellow solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. custominsoluble were removed by filtration
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. washafter washed with 1.0 mol/L hydrochloric acid
  6. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated, under reduced pressure
  7. additionHexane and diisopropyl ether were added to the obtained residue
  8. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-eb76f654ed4b4b3db12b5f7abefe8bfe
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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