Ethyl Acetate → 4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol

Participants

Reaction Steps

A solution of intermediate 11 (0.0031 mol), N,N-diisopropylethylamine (0.0028 mol), 4-bromopyridine hydrochloride (0.0034 mol) in acetonitrile (20 ml) was heated at 65° C. for 6 hours. Potassium carbonate 10% and EtOAc were added. The reaction mixture was extracted, the organic layer was separated, dried over MgSO4, filtered and concentrated. The residue (1.3 g) was purified by column chromatography over silica gel (eluent 95/5/0.5 DCM/MeOH/NH4OH). Two fractions were collected and the solvent was evaporated to give 60 mg of compound 3 and 80 mg of F2. The residue F2 (80 mg) was purified by supercritical fluid chromatography (AMINO column 150×21.2 mmm) eluent: MeOH/CO2 30/70). The pure fractions were collected and the solvent was evaporated, yielding 43 mg of compound 2.

Provenance & Evidence