Premium
Preparation of carbon‐14 labeled 3,4‐dihydro‐5‐methyl‐1(2H)‐isoquinolinone
Author(s) -
Ekhato I. Victor,
Huang Che C.
Publication year - 1994
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.2580340706
Subject(s) - chemistry , curtius rearrangement , carboxylation , isocyanate , yield (engineering) , azide , stereochemistry , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy , polyurethane
Carbon‐14 labeled 3,5‐dihydro‐5‐methyl‐1(2H)‐isoquinolinone, a potent inhibitor of poly(ADP‐ribose) polymerase (ADPRP) was prepared from 1‐bromo‐2‐methylbenzene in 7.8 % overall yield. The C‐14 label was introduced from Ba 14 CO 3 via metal‐halogen exchange and carboxylation reactions. Subsequent transformations yielded a propenecarbonyl azide 8 which was rearranged by Curtius reaction to the isocyanate, and a cyclization produced 5‐methyl‐1(2H)‐[4‐ 14 C]isoquinolinone ( 9 ). From the compound 9 by Pd/C catalyzed hydrogenation 3,4‐dihydro‐5‐methyl‐1(2H)‐[4‐ 14 C]isoquinolinone ( 10 ) was made.