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18. Typical procedure of the cross-coupling reaction: To a
solution mixture of halo-compound (6.53 mmol, 1 equiv)
in DME (40 mL) under argon was added Pd(PPh3)4
(0.32 mmol, 0.05 equiv) followed by the addition of 1-
THP-1H-pyrazolylboronic ester (7.19 mmol, 1.1 equiv)
and sodium hydrogen carbonate (13 mmol, 2 equiv) in
H2O (25 mL). The reaction mixture was refluxed and the
rate of the reaction, followed by TLC. After the starting
halo-compound was consumed, the organic solvent was
removed under reduced pressure. The residue was
extracted with AcOEt and the organic layer was
dried (MgSO4) and evaporated. The crude products
were purified by column chromatography (AcOEt/
cyclohexane).
19. Typical procedure of deprotection: A solution of 8 (2 mmol)
in EtOH (5 mL) was treated with ethanolic HCl (10 mL)
and stirred for 1 h at room temperature. After neutraliza-
tion with aqueous sodium bicarbonate, the residue was
extracted with AcOEt and the organic layer was dried
(MgSO4). The solvent was removed and the crude product
was purified by column chromatography (AcOEt/
cyclohexane).
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