Phenylacetylene → {4-[3-(2-Cyclohexyl-ethoxy)-5-phenylethynyl-phenylsulfanyl]-2-methylphenoxy}-acetic Acid Ethyl Ester

HRID 1969258Notes

Reaction equation

HRID 1969258 reaction equation
C(OC(=O)COC1C=CC(SC2C=C(OCCC3CCCCC3)C=C(Br)C=2)=CC=1C)C.C1(C#C)C=CC=CC=1.[CH2:40]([O:42][C:43](=[O:80])[CH2:44][O:45][C:46]1[CH:51]=[CH:50][C:49]([S:52][C:53]2[CH:58]=[C:57]([C:59]#[C:60][C:61]3[CH:66]=[CH:65][C:64](CO)=[CH:63][CH:62]=3)[CH:56]=[C:55]([O:69][CH2:70][CH2:71][C:72]3[CH:77]=[CH:76][C:75](Cl)=[CH:74][CH:73]=3)[CH:54]=2)=[CH:48][C:47]=1[CH3:79])[CH3:41]>>[CH2:40]([O:42][C:43](=[O:80])[CH2:44][O:45][C:46]1[CH:51]=[CH:50][C:49]([S:52][C:53]2[CH:58]=[C:57]([C:59]#[C:60][C:61]3[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=3)[CH:56]=[C:55]([O:69][CH2:70][CH2:71][CH:72]3[CH2:77][CH2:76][CH2:75][CH2:74][CH2:73]3)[CH:54]=2)=[CH:48][C:47]=1[CH3:79])[CH3:41]

Participants

4

Reactant 3

HCID 10821PhenylacetyleneHCID 57791911{4-[3-Bromo-5-(2-cyclohexyl-ethoxy)phenylsulfanyl]-2-methyl-phenoxy}-acetic acid ethyl esterHCID 67024299{4-[3-[2-(4-Chloro-phenyl)-ethoxy]-5-(4-hydroxymethyl-phenylethynyl)-phenylsulfanyl]-2-methylphenoxy}-acetic acid ethyl ester

Product 1

HCID 67169780{4-[3-(2-Cyclohexyl-ethoxy)-5-phenylethynyl-phenylsulfanyl]-2-methylphenoxy}-acetic Acid Ethyl Ester

Procedure

The title product was prepared from {4-[3-Bromo-5-(2-cyclohexyl-ethoxy)-phenylsulfanyl]-2-methyl-phenoxy}-acetic acid ethyl ester (300 mg; 0.58 mmol), phenylacetylen (181.1 mg; 1.8 mmol) applying the procedure described for {4-[3-[2-(4-Chloro-phenyl)-ethoxy]-5-(4-hydroxymethyl-phenylethynyl)-phenylsulfanyl]-2-methyl-phenoxy}-acetic acid ethyl ester. The crude product was purified by preparative HPLC (method B). Yield: 110 mg (33%). HPLC-MS: m/z: 529.6 (M+H)+; Rt: 3.38 min.

Workup

  1. customThe crude product was purified by preparative HPLC (method B)

Sources & evidence

ORD record
ord-8160b89b561c45e59cce0d3e82d7a9a5
Source dataset
uspto-grants-2013_04
Patent number
US08426473B2

Reaction notes

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