Mitsunobu coupling of N-Boc-3-(S)-hydroxypyrrolidine (I) with 3-bromo-2-chloro-5-hydroxypyridine (II) afforded ether (III). Subsequent introduction of the cyanophenyl group in (III) to give (V) was effected by Suzuki coupling with boronic acid (IV) in the presence of palladium catalyst. Finally, acid deprotection of the Boc group of (V) furnished the title compound.

Mitsunobu coupling of N-Boc-3-(S)-hydroxypyrrolidine (I) with 3-bromo-2-chloro-5-hydroxypyridine (II) afforded ether (III). Subsequent introduction of the cyanophenyl group in (III) to give (V) was effected by Suzuki coupling with boronic acid (IV) in the presence of palladium catalyst. Finally, acid deprotection of the Boc group of (V) furnished the title compound.

The compound has also been obtained by solid phase synthesis. Attachment of (S)-3-hydroxypyrrolidine (VII) to p-nitrophenylcarbonate Wang resin (VI) in the presence of diisopropylethylamine provided the resin bound pyrrolidinol (VIII). Coupling of (VIII) with 3-bromo-2-chloro-5-hydroxypyridine (II) under Mitsunobu conditions gave resin (IX). Further Suzuki coupling of (IX) with 4-cyanophenylboronic acid (IV) afforded (X). The title compound was then cleaved from the resin (X) by treatment with trifluoroacetic acid.

The compound has also been obtained by solid phase synthesis. Attachment of (S)-3-hydroxypyrrolidine (VII) to p-nitrophenylcarbonate Wang resin (VI) in the presence of diisopropylethylamine provided the resin bound pyrrolidinol (VIII). Coupling of (VIII) with 3-bromo-2-chloro-5-hydroxypyridine (II) under Mitsunobu conditions gave resin (IX). Further Suzuki coupling of (IX) with 4-cyanophenylboronic acid (IV) afforded (X). The title compound was then cleaved from the resin (X) by treatment with trifluoroacetic acid.