2-Bromo-3-chloropyridine → HCID 178418209, compound

Participants

Reaction Conditions

Reaction Steps

Pd2(dba)3 (0.018 g, 0.02 mmol), 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (0.024 g, 0.04 mmol) and toluene (4 mL) was added to a flask. 2-bromo-3-chloropyridine (0.5 g, 2.60 mmol), 1-methylazetidin-3-amine hydrochloride (0.414 g, 3.38 mmol) and sodium 2-methylpropan-2-olate (0.624 g, 6.50 mmol) was added, the mixture bubbled with N2 for 5 min, then the reaction was heated to 115 °C in an oil-bath under nitrogen for 2h, then to rt over night. The reaction was cooled to rt and the solvent was evaporated. The residue was purified by automated flash chromatography on a 100g column. A gradient from 10% to 100% of EtOAc (with 2% TEA) in heptane over 25CV was used as mobile phase. The product was collected using the wavelength 243 and 308 nm. No product found in any fractions. Reaction discarded.

Provenance & Evidence