5-Bromo-2-(2-pyrrolidinyl)pyridine

Step 1 Preparation of 2-(5-Bromo-pyridin-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester A solution of 5-Bromo-2-pyrrolidin-2-yl-pyridine (611 mg, 2.69 mmol) (previously described in WO200853319) in CH2Cl2 (20 ml) is treated with di-tert-butyl dicarbonate (881 mg, 4.04 mmol) and triethylamine (0.562 ml, 4.04 mmol), and stirred at ambient temperature for 16 hours. The reaction mixture is washed with 10percent aqueous citric acid solution (25 ml). The organic phase is concentrated on to silica gel (5 g) and purified by column chromatography (40 g silica gel, ethyl acetate/heptane 0-50percent) to afford the title compound (500 mg): 1H NMR (400 MHz, CDCl3) 1.23 (s, 5H), 1.4 5 (s, 4H), 1.82-2.09 (m, 3H), 2.24-2.43 (m, 1H), 3.47-3.74 (m, 2H), 4.67-4.99 (m, 1H), 7.05-7.14 (m, 1H), 7.71-7.78 (m, 1H), 8.59 (dd, 1H). m/z M+H 327.

Molecular Weight:227.10
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:226.01056
Monoisotopic Mass:226.01056
Topological Polar Surface Area:24.9
Heavy Atom Count:12
Complexity:152
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes