5H-Cyclopenta[b]pyridine, 4-chloro-6,7-dihydro-

6, 7-Dihydro-5H-cyclopenta[b]pyridine 1-oxide (2.5 g, 18 mmol) was mixed with phosphoryl chloride (20 mL, 200 mmol). The reaction mixture was stirred at 120° C. for 3 h. The excess POCl6, 7-Dihydro-5H-cyclopenta[b]pyridine 1-oxide (2.5 g, 18 mmol) was mixed with POCl6, 7-Dihydro-5H-cyclopenta[Z>]pyridine 1-oxide (2.5 g, 18 mmol) was mixed with POCh (20 mL). The reaction mixture was stirred at 120 °C for 3 h. The excess POCh was removed under reduced pressure. The residue was dissolved in EtOAc (80 mL) and neutralized with aq. Na2C03. After filtration, the aqueous layer was extracted with EtOAc twice. The combined organic layers were dried, filtered and concentrated under reduced pressure to give the sub-title compound (2.6 g, 93percent). LCMS calc. for CsHoClN (M+H)b- A mixture of 4-chloro-6, 7-dihydro-5H-cyclopenta[Z>]pyridine (2.8 g, 18 mmol), MeOH (20 mL) and sodium methoxide (3.0 g, 56 mmol) was sealed in a pressurized flask and heated at 1 10 C for 18 h. The mixture was diluted with EtOAc and neutralized with HCl to pH = 1. The organic solvent was removed under reduced pressure. The resulting mixture was washed with ether twice, and then neutralized with Na2C03 solution. The aqueous layer was extracted twice with EtOAc. The combined organic layers were dried, filtered and concentrated under reduced pressure to give the sub-title compound (1.20 g, 44%). LCMS calc. for C9H12NO (M+H)+: m/z = 150.1. Found: 150.2.

Molecular Weight:153.61
XLogP3:2.2
Hydrogen Bond Acceptor Count:1
Exact Mass:153.0345270
Monoisotopic Mass:153.0345270
Topological Polar Surface Area:12.9
Heavy Atom Count:10
Complexity:126
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes