Triethylamine → HCID 49765145, compound

HRID 2390320Notes

Reaction equation

HRID 2390320 reaction equation
C([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1Br)(C)(C)C.[C:18]1([C:24]#[CH:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.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.C(#N)C>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]([OH:5])=[O:17])=[C:10]([C:25]#[C:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 49766393tert-Butyl (2-bromo-4-chlorophenoxy)acetate

Product 1

HCID 49765145HCID 49765145, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A solution of tert-butyl(2-bromo-4-chlorophenoxy)acetate (350 mg; 1.09 mmol) and phenylacetylene (Aldrich; 122 mg; 1.20 mmol) in degassed, anhydrous ACN (2.80 mL) was treated with dichlorobis(triphenylphosphine)palladium(II) (38 mg; 0.05 mmol), copper(I) iodide (10 mg; 0.05 mmol) and triethylamine (0.45 mL; 3.26 mmol). The reaction mixture was heated at 50° C. under stirring for 16 hours. The solvent was evaporated, the residue dissolved in DCM (4 mL) and TFA (1 mL) was added. After stirring for 45 minutes, the solvents were removed under vacuum and the crude product purified by preparative HPLC. The title compound was obtained as a brown solid.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in DCM (4 mL)
  3. additionTFA (1 mL) was added
  4. stirringAfter stirring for 45 minutes
  5. customthe solvents were removed under vacuum
  6. customthe crude product purified by preparative HPLC

Sources & evidence

ORD record
ord-70c9dc168b494b5f895fc9e9b5d5810a
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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