Hydrochloric Acid → HCID 69086111, compound

Participants

Reaction Conditions

Reaction Steps

A 10 mL vial is charged with 2-Chloro-4-[2-(4-fluoro-phenyl)-2H-pyrazol-3-yl]-pyridine (160 mg, 0.59 mmol), Tris(dibenzylideneacetone)dipalladium (54 mg, 0.058 mmol) and 2-(dicyclohexylphosphino)biphenyl (53.3 mg, 0.15 mmol) in dry THF (3 mL) and Argon is bubbled through the mixture for 5 min. Additional THF (1 mL) and LiHMDS (1M in toluene, 1.14 mL, 1.5 mmol) are added and the reaction mixture is heated at 65° C. for 14 hours. Then 5 mL of 3.0 M HCl solution is added and the mixture is stirred for 10 min. Additional water (10 mL) is added and the mixture is extracted with EtOAc (2×10 mL). The aqueous layer is separated and its pH is adjusted to 10 by adding saturated Na2CO3 aquaous solution. The mixture is then extracted with EtOAc three times and the organic layers are combined, washed with brine and dried over anhdrous Na2SO4. Removal of solvent gives the desired product (83 mg).

Provenance & Evidence