Triethylamine → HCID 56594263, compound

HRID 2390325Notes

Reaction equation

HRID 2390325 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]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[F:27])#[CH:19].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.CC#N>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]([OH:5])=[O:17])=[C:10]([C:19]#[C:18][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[CH:11]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 50638201-Ethynyl-2,4-difluorobenzeneHCID 49766393tert-Butyl (2-bromo-4-chlorophenoxy)acetate

Product 1

HCID 56594263HCID 56594263, 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 1-ethynyl-2,4-difluorobenzene (Aldrich, 165 mg; 1.20 mmol) in degassed, anhydrous CH3CN (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 and the residue dissolved in DCM (1 mL) and an HCl solution (4 N in dioxane, 2.7 mL) was added. After stirring for 16 hours, the solvents were removed under vacuum and the crude product purified by preparative HPLC. The title compound was obtained as an off-white solid.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in DCM (1 mL)
  3. additionan HCl solution (4 N in dioxane, 2.7 mL) was added
  4. stirringAfter stirring for 16 hours
  5. customthe solvents were removed under vacuum
  6. customthe crude product purified by preparative HPLC

Sources & evidence

ORD record
ord-6129307e2d61465b9dc54076741e185d
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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