Benzylacetylene → [4-(3-hydroxy-5-phenylethynyl-phenylsulfanyl)-2-methyl-phenoxy]-acetic Acid Ethyl Ester

HRID 1969191Notes

Reaction equation

HRID 1969191 reaction equation
[CH2:1]([O:3][C:4](=[O:6])[CH3:5])[CH3:2].Br[C:8]1[CH:9]=[C:10]([S:15][C:16]2[CH:26]=[CH:25][C:19]([O:20]CC(O)=O)=[C:18]([CH3:27])[CH:17]=2)[CH:11]=[C:12]([OH:14])[CH:13]=1.[C:28]1([CH2:34][C:35]#C)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(N(CC)CC)C.CN(C=O)C.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.[Cu](I)I>[CH2:1]([O:3][C:4](=[O:6])[CH2:5][O:20][C:19]1[CH:25]=[CH:26][C:16]([S:15][C:10]2[CH:9]=[C:8]([C:35]#[C:34][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:13]=[C:12]([OH:14])[CH:11]=2)=[CH:17][C:18]=1[CH3:27])[CH3:2]

Participants

7

Reactant 2

HCID 575753BenzylacetyleneHCID 67024264[4-(3-Bromo-5-hydroxy-phenylsulfanyl)-2-methyl-phenoxy]-acetic Acid Ethyl Acetate

Product 1

HCID 57791909[4-(3-hydroxy-5-phenylethynyl-phenylsulfanyl)-2-methyl-phenoxy]-acetic Acid Ethyl Ester

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

[4-(3-Bromo-5-hydroxy-phenylsulfanyl)-2-methyl-phenoxy]-acetic acid ethyl acetate (3 g; 7.55 mmol), 3-phenyl-1-propyn (2.63 g; 22.65 mmol), bis(triphenylphosphine)palladium (II) chloride (0.42 g; 0.60 mmol) and copper iodide (0.086 g; 0.45 mmol) were dissolved in a mixture of triethylamine (3 mL) and DMF (6 mL) under an atmosphere of nitrogen. The reaction mixture was reacted in a microwave oven at 100° C. for 11 h. The reaction mixture was evaporated to dryness, and portioned between 5% aqueous citric acid and ethyl acetate. The organic phase was dried and evaporated to dryness. The crude product was purified by preparative HPLC method A. Yield: 1.4 g. HPLC-MS: m/z: 433.3 (M+); Rt: min.

Workup

  1. customThe reaction mixture was reacted in a microwave oven at 100° C. for 11 h
  2. customThe reaction mixture was evaporated to dryness
  3. customThe organic phase was dried
  4. customevaporated to dryness
  5. customThe crude product was purified by preparative HPLC method A

Sources & evidence

ORD record
ord-c11cbabb120e4e67bcf83cea4a2d4f3f
Source dataset
uspto-grants-2013_04
Patent number
US08426473B2

Reaction notes

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