Triethylamine → HCID 46865875, compound

HRID 2390326Notes

Reaction equation

HRID 2390326 reaction equation
Br[C:2]1[S:3][C:4]([Cl:7])=[CH:5][CH:6]=1.C([O:12][C:13](=[O:25])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[C:23]#[CH:24])(C)(C)C.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.C1COCC1>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH2:14][C:13]([OH:25])=[O:12])=[C:17]([C:23]#[C:24][C:2]2[S:3][C:4]([Cl:7])=[CH:5][CH:6]=2)[CH:18]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 761332-Bromo-5-chlorothiopheneHCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2×

Product 1

HCID 46865875HCID 46865875, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
60 °C

Procedure

A mixture of 2-bromo-5-chlorothiophene (Aldrich, 163 mg; 0.82 mmol), tert-butyl(4-chloro-2-ethynylphenoxy)acetate (Intermediate 3, 200 mg; 0.75 mmol), dichlorobis(triphenylphosphine)palladium(II) (33 mg; 0.04 mmol), copper(I) iodide (8.6 mg; 0.04 mmol) was degassed during two minutes under nitrogen then THF (3 mL) and triethylamine (208 μL; 1.50 mmol) were added and reaction mixture was stirred at 60° C. for 16 hours. The solvent was evaporated and the residue was treated with an HCl solution (4 N in dioxane, 3.7 mL). 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 a brown sticky solid.

Workup

  1. customwas degassed during two minutes under nitrogen
  2. customreaction mixture
  3. customThe solvent was evaporated
  4. additionthe residue was treated with an HCl solution (4 N in dioxane, 3.7 mL)
  5. stirringAfter stirring for 16 hours
  6. customthe solvents were removed under vacuum
  7. customthe crude product purified by preparative HPLC

Sources & evidence

ORD record
ord-0810f878e39d443c89f8dcba88d4119d
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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