Under nitrogen flow, 4'-Chloroacetophenone (200 mg, 1.29 mmol) and 1-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester (440 mg, 1.42 mmol) were dissolved in a mixture of toluene (5.0 mL), EtOH (2.0 mL) and H₂O (2.0 mL). To this solution was added K₃PO₄ (820 mg, 3.88 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos) (21 mg, 0.052 mmol, 4 mol%) and tris(dibenzylideneacetone)dipalladium(0) (18 mg, 0.020 mmol, 1.5mol%). The reaction mixture was refluxed for 21 h under nitrogen flow. Then allowed to cool to room temperature and quenched with H₂O (2.0 ml). The organic phase was separated and washed with H₂O (5 mL) and brine (5 mL), dried over Na₂SO₄ (10 g), and concentrated under reduced pressure to afford the crude product as orange oil. It was purified by column chromatography on silica-gel (Hexane 100% to Hexane: EtOAc = 70: 30) to afford the product as colorless crystalline solid (310 mg, 1.03 mmol, 80%).

 ¹H NMR (400 MHz, CDCl₃) δ 7.90 (d, J = 8.7 Hz, 2H), 7.42 (d, J = 8.7 Hz, 2H), 6.15 (brs, 1H), 4.08 (m, 2H), 3.63 (m, 2H), 2.50 (s, 3H), 2.52 (m, 2H), 1.47 (s, 9H).

Same compound was synthesized from Aryl bromide.
(1) Kim, Ronald M.; et al, Preparation of pyrazolecarboxylic acid derivatives as soluble guanylate cyclase activators, U. S. Patent, 20100216764 A1 2010-08-26