Diisobutylaluminum hydride → (6-(3,4-Dichlorobenzylamino)pyridin-3-yl)methanol

A solution of methyl 6-((3,4-dichlorobenzyl)amino)nicotinate (0.88 g, 2.83 mmol) in THF (18.9 mL) was cooled to −78° C. and a 1M solution of DIBAL-H (14.14 mL, 14.14 mmol) in toluene was added. The mixture was stirred for 1.5 h while warming to room temperature. The reaction mixture was diluted with THF (20 mL) and quenched with Na2SO4.10H2O followed by a few drops of water. The mixture was stirred at room temperature for 18 h, then filtered through a pad of Celite topped with silica gel. The pad was washed with ethyl acetate and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel using 45-80% ethyl acetate in hexanes. The desired fractions were concentrated to give (6-(3,4-dichlorobenzylamino)pyridin-3-yl)methanol as a white solid (0.46 g, 57%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.91 (1H, d, J=1.76 Hz), 7.40-7.52 (3H, m), 7.26 (1H, dd, J=8.28, 2.01 Hz), 6.51-6.59 (1H, m), 4.50 (2H, s), 4.44 (2H, s). LCMS: R.T.=2.74; [M+H]+=282.99.

1. customquenched with Na2SO4.10H2O
2. stirringThe mixture was stirred at room temperature for 18 h
3. filtrationfiltered through a pad of Celite
4. washThe pad was washed with ethyl acetate
5. concentrationthe filtrate was concentrated
6. customThe residue was purified by flash chromatography on silica gel using 45-80% ethyl acetate in hexanes
7. concentrationThe desired fractions were concentrated

ORD record

ord-0d751036c69049e98f5ede8a808db946

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841301B2