Phenylacetylene → HCID 67170143, compound

HRID 549607Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:29])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[C:18]([O:20][CH2:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[CH:17]=[C:16](Br)[CH:15]=2)=[CH:9][C:8]=1[CH3:28])[CH3:2].[C:30]1([C:36]#[CH:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(OC(=O)COC1C=CC(SC2C=C(C#CC3C=CC(CO)=CC=3)C=C(OCCC3C=CC(Cl)=CC=3)C=2)=CC=1C)C>>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:15]=[C:16]([C:37]#[C:36][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:17]=[C:18]([O:20][CH2:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[CH:19]=2)=[CH:9][C:8]=1[CH3:28])[CH3:2]

Participants

Reactant 3

HCID 10821Phenylacetylene

HCID 57791914HCID 57791914, compound

HCID 67024299{4-[3-[2-(4-Chloro-phenyl)-ethoxy]-5-(4-hydroxymethyl-phenylethynyl)-phenylsulfanyl]-2-methylphenoxy}-acetic acid ethyl ester

Product 1

HCID 67170143HCID 67170143, compound

Procedure

The title product was prepared from {4-[3-Bromo-5-(2-ethyl-butoxy)-phenylsulfanyl]-2-methyl-phenoxy}-acetic acid ethyl ester (200 mg; 0.42 mmol), (phenyl acetylene (170 mg; 1.66 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: 170 mg (82%). HPLC-MS: m/z: 502.9 (M)+; Rt: 3.32 min.

Workup

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

Sources & evidence

ORD record: ord-45b097b9884340169a9cd785c3f256eb
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943669B2

Reaction notes

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