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%).

All chemical manipulations were performed in a fume hood. 
Before adding the reagents, mixture of toluene, EtOH and water was degassed by refluxing for 10 minute under nitrogen flow then cooled to room temperature.
This procedure is typical for Suzuki-Miyaura cross coupling reaction of Aryl chlorides.
Pd₂(dba)₃-SPhos can also be adapted to the Suzuki-Miyaura cross-coupling reaction of aryl chlorides having electron-donating or bulky substitutents.

 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

1H-NMR