Ammonium Chloride → HCID 21097263, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-4-trimethylsilanylethynyl-pyridine (9.3 g, 44 mmol), tris(dibenzylideneacetone)dipalladium(0) (8.1 g, 8.9 mmol) and 2-(dicyclohexylphosphino)biphenyl (8.1 g, 23 mmol) are added into the de-gased dry THF (60 mL). Then 1.0 M LiHMDS (155 mL, 155 mmol) is added. The reaction mixture is heated at 60° C. for 16 hrs before it is cooled down to room temperature and saturated NH4Cl aqueous solution (100 mL) is added along with water (100 mL). The mixture is extracted with EtOAc (2×200 mL) and the organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using 33% EtOAc in hexanes affords 7.9 g of the desired product.

Provenance & Evidence