Ammonium Chloride → HCID 69083700, compound

Participants

Reaction Steps

2-Bromo-4-[5-(4-fluoro-phenyl)-3-methyl-3H-imidazol-4-yl]-pyridine (460 mg, 1.39 mmol), tris(dibenzylideneacetone)dipalladium(0) (254 mg, 0.28 mmol) and 2-(dicyclohexylphosphino)biphenyl (252 mg, 0.72 mmol) are mixed in dry THF (10 mL). Then Argon is bubbled through the solution for 5 min and 1.0 M LiHMDS (4.8 mL, 4.8 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 (25 mL). The mixture is extracted with EtOAc (3×50 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%) followed by Gilson preparative HPLC affords 15 mg of desired product.

Provenance & Evidence