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A chemical probe for the estrogen receptor: Synthesis of the 3 H‐isotopomer of raloxifene
Author(s) -
Dodge Jeffrey A.,
Stocksdale Mark G.,
Jones C. David
Publication year - 1995
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580360105
Subject(s) - chemistry , hydrogenolysis , raloxifene , benzothiophene , regioselectivity , chemical synthesis , tritium , benzoic acid , catalysis , alkoxy group , aryl , medicinal chemistry , halogen , organic chemistry , stereochemistry , estrogen receptor , alkyl , biochemistry , medicine , physics , cancer , breast cancer , nuclear physics , in vitro , thiophene
Radiolabelled raloxifene (LY156758) has been prepared by tritium gas hydrogenolysis of a 3‐aroyl‐ bis ‐brominated precursor. The requisite halogenated intermediate was accessed by regioselective aroylation of benzothiophene 6 with the acid chloride of 3,5‐dibromo‐4‐[2‐(1‐piperdinyl)ethoxy]benzoic acid ( 5 ). Selective deprotection of the aryl methyl ethers in the presence of the ethoxy side‐chain followed by palladium catalyzed halogen‐tritium exchange provided the target compound with a specific activity of 30.1 Ci/mmol.