Ammonium Chloride → HCID 69083084, compound

Participants

Reaction Steps

2-Bromo-4-[2-(3-trifluoromethyl-phenyl)-vinyl]-pyridine (289 mg, 0.88 mmol), tris(dibenzylideneacetone)dipalladium(0) (160 mg, 0.18 mmol) and 2-(dicyclohexylphosphino)biphenyl (160 mg, 0.46 mmol) are mixed in dry THF (6 mL). Then Argon is bubbled through the solution for 5 min and 1.0 M LiHMDS (3.1 mL, 3.1 mmol) is added. Then the reaction mixture is heated at 65° C. for 16 hrs before the saturated NH4Cl aqueous solution (20 mL) is added along with water (30 mL). The mixture is extracted with EtOAc (3×35 mL) and the organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using MeOH in DCM (gradient from 0% to 10%) affords 193 mg of the desired product.

Provenance & Evidence