Cyclopentylamine → N-Cyclopentyl-5-nitropyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a 20 mL vial containing cyclopentylamine (300 mg, 3.53 mmol) was added DMF (5 mL), 2-chloro-5-nitro-pyridine (559 mg, 3.53 mmol), and the TEA (0.98 mL). The vessel was purged with argon, sealed, and heat by microwave at 200° C. for 5 min (Personal Chemistry, Emrys Optimizer). The reaction mixture was concentrated, diluted with water (100 mL) and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate (100 mL) and brine (100 mL), dried over sodium sulfate, and evaporated to give cyclopentyl-(5-nitro-pyridin-2-yl)-amine. LCMS calcd. C10H13N3O2 (m/e) 207, observed 208 (M+H). This intermediate nitropyridyl compound was transferred to a PARR vessel with MeOH (5 mL), Pd/C (10%) was added and the vessel was pressurized with H2 at 55 psi and shaken for 2.5 hr. The mixture was then filtered through a bed of celite and concentrated to dryness twice from CH2Cl2. The purple black material was used immediately for amide coupling (LCMS calcd. for C10H15N3 (m/e) 177, observed 178 (M+H).

Provenance & Evidence