Allylamine → Hydrochloric Acid

Participants

Reaction Conditions

Reaction Steps

To a preformed bright-yellow complex of Pd(dppf)Cl2CH2Cl2 (41 mg, 0.05 mmol), dppf (83 mg, 0.15 mmol) and NaOt-Bu (1.4 g, 15 mmol) in THF (20 mL) was added 2-chloro-3-fluoropyridine (1.32 g, 10 mmol) and allylamine (1.2 mL, 15 mmol). The mixture was sparged with nitrogen and the pressure vessel was capped and sealed. The reaction was heated at 65-70° C. for 16 hours. The cooled reaction was filtered through a plug of Celite and the pad was washed with EtOAc (30 mL). The solvent was removed under reduced pressure to give a brown thick oil. The crude product was purified by silica gel chromatography eluting with 5% MeOH in EtOAc. The product-containing fractions were diluted with EtOAc (100 mL) and extracted with 1 M HCl (2×50 mL). The aqueous acidic product was lyophilized to a light brown solid giving N-allyl-3-fluoropyridin-2-amine as an HCl salt (1.6 g, 85%). LC/MS (m/z): 153.1 (MH+), Rt 0.5 minutes.

Provenance & Evidence