Trimethylsilylacetylene → Ethyl 2-(4-amino-2-chloro-5-((trimethylsilyl)ethynyl)phenoxy)-4-fluorobenzoate

HRID 1043116Notes

Reaction equation

HRID 1043116 reaction equation
[NH2:1][C:2]1[C:20](I)=[CH:19][C:5]([O:6][C:7]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:8]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([Cl:22])[CH:3]=1.[CH3:23][Si:24]([C:27]#[CH:28])([CH3:26])[CH3:25]>C(N(CC)CC)C.C(OCC)(=O)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>[NH2:1][C:2]1[C:20]([C:28]#[C:27][Si:24]([CH3:26])([CH3:25])[CH3:23])=[CH:19][C:5]([O:6][C:7]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:8]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([Cl:22])[CH:3]=1

Participants

7

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 67228200Ethyl 2-(4-amino-2-chloro-5-iodophenoxy)-4-fluorobenzoate

Product 1

HCID 67226491Ethyl 2-(4-amino-2-chloro-5-((trimethylsilyl)ethynyl)phenoxy)-4-fluorobenzoate

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of EXAMPLE 242B (3.0 g), bis(triphenylphosphine)palladium(II) dichloride (242 mg), CuI (66 mg) in triethylamine (30 mL) was added trimethylsilylacetylene (2.2 g). The mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate (200 mL) and washed with aqueous NH4Cl, water, brine and dried over Na2SO4. The mixture was filtered, and the solvent was evaporated and the residue was loaded on a column and eluted with 10% ethyl acetate in hexane to give the pure product.

Workup

  1. washwashed with aqueous NH4Cl, water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationThe mixture was filtered
  4. customthe solvent was evaporated
  5. washeluted with 10% ethyl acetate in hexane
  6. customto give the pure product

Sources & evidence

ORD record
ord-7435f0486dbc419b91a7420b2b2ebd8b
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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