Ammonium Chloride → 4-[2-(4-Fluoro-phenyl)-cyclohex-1-enyl]-pyridin-2-ylamine

Participants

Reaction Conditions

Reaction Steps

A sealed 8 mL vial is charged with 2-Chloro-4-[2-(4-fluoro-phenyl)-cyclohex-1-enyl]-pyridine (25 mg, 0.087 mmol), Tris(dibenzyldieneacetone)Dipalladium (15.9 mg, 0.017 mmol) and 2-(dicyclohexylphosphino)biphenyl (15.8 mg, 0.045 mmol) in dry THF (3 mL). Argon is bubbled through the mixture for 5 min. Additional THF (1 mL) and LiHMDS (1.0 M in toluene, 0.26 mL, 0.26 mmol) are added. And the resulting mixture is allowed to stir at 65° C. for 1 hour. To the mixture is added saturated ammonium chloride solution and extracted with EtOAc (10 mL×3). The organic extract are washed with water (10 mL×1) and brine (10 mL×1), and dried over anhydrous sodium sulfate. After concentration, the crude is purified by silica flash column chromatography using MeOH in DCM (gradient from 0% to 10%) to give 11 mg of the desired product.

Provenance & Evidence