Ammonium Chloride → HCID 69083646, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-4-[2-(4-fluoro-phenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-pyridine (120 mg, 0.35 mmol), Pd2(dba)3 (32 mg, 0.04 mmol) and biphenyl-2-yl-dicyclohexyl-phosphane (32 mg, 0.09 mmol) are mixed in a reaction vial and dry THF (2.0 mL) is added. Then Argon is bubbled through the solution for 5 min and 1.0 M LiHMDS (0.88 mL, 0.88 mmol) in THF is added. The reaction vial is sealed and heated at 65° C. for 16 hrs. More Pd2(dba)3 (32 mg, 0.04 mmol), biphenyl-2-yl-dicyclohexyl-phosphane (32 mg, 0.09 mmol) and 1.0 M LiHMDS (0.88 mL, 0.88 mmol) in THF are added and the reaction mixture is heated at 65° C. for another 5 hrs. Then saturated NH4Cl solution (20 mL) is added along with water (20 mL). The mixture is extracted with EtOAc (3×30 mL) and the organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography using MeOH in DCM (gradient from 0% to 10%) affords 107 mg of product.

Provenance & Evidence