(3-CHLOROPYRIDIN-2-YL)METHANOL

To a solution of 3-chloropyridine-2-carboxylic acid (2.1 g, 13.33 mmol, 1.00 equiv) in THF (40 mL) was added EtMethyl 1-[(3-chloropyridin-2-yl)methyl]-5-(3-methoxyphenyl)-1H-pyrazole-3-carboxylate To a solution of the product from the previous step (850 mg, 5.92 mmol, 1.00 equiv) in THF (8.5 mL), under N2, was added Int. D-3 (1.4 g, 6.03 mmol, 1.00 equiv) and Ph3P (3.1 g, 11.82 mmol, 2.00 equiv), followed by the addition of DIAD (1.8 g, 8.91 mmol, 1.50 equiv) dropwise with stirring at 0° C. The resulting solution was stirred for 5 h at rt, diluted with 30 mL of H2O, and extracted with 2*50 mL of EtOAc. The combined organic layers were washed with 20 mL of saturated Nacl, dried over Na2SO4, concentrated under vacuum, and purified with silica gel chromatography using EtOAc/petroleum ether (1:10) to afford 1.7 g (80percent) of the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) delta 8.90 (s, 1H), 8.35 (dd, J=4.7, 1.5 Hz, 1H), 7.99 (dd, J=8.1, 1.5 Hz, 1H), 7.51 (s, 1H), 7.45 (dt, J=7.7, 1.2 Hz, 1H), 7.41 (dd, J=2.6, 1.5 Hz, 1H), 7.36-7.30 (m, 1H), 6.91 (ddd, J=8.2, 2.7, 1.0 Hz, 1H), 5.99 (s, 2H), 3.80 (s, 3H), 3.77 (s, 3H).General procedure: Freshly prepared Ag2O (2.20 mmol) was added at room temperature to a solution of pyridin-2-ylmethanol (1.00 mmol) and 2-iodopropane (2.20 mmol) in 1, 4-dioxane (10 mL) and stirred for 24 h. The reaction mixture was filtered through a Celite bed and washed with ethyl acetate. Filtrate was concentrated under vacuum.The resulting material was purified by flash chromatography on a Biotage instrumentusing 4-g flash cartridge and eluted with 12'15percent ethyl acetate in hexane to give isopropyl picolinate (2) (65percent yield).

Molecular Weight:143.57
XLogP3:0.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:143.0137915
Monoisotopic Mass:143.0137915
Topological Polar Surface Area:33.1
Heavy Atom Count:9
Complexity:89.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes