Cyclobutylamine → 3-chloro-N-cyclobutylpyridin-2-amine

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Pd2(dba)3 (0.014 g, 0.02 mmol), 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (0.019 g, 0.03 mmol) and toluene (8 mL) was added to a flask. 2-bromo-3-chloropyridine (0.4 g, 2.08 mmol), cyclobutanamine (0.177 g, 2.49 mmol) and sodium 2-methylpropan-2-olate (0.348 g, 3.62 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. LC-MS 1h: 33% product, 21% sm left. The reaction was cooled to rt and the solvent was evaporated. The residue was purified by automated flash chromatography on a 50g column. A gradient from 0% to 50% of EtOAc in heptane over 15CV was used as mobile phase. The product was collected using the wavelength 245 and 311 nm, relevant fractions pooled and evaporated to give 95 mg clear oil. 1H-NMR: OK, some extra small peaks in aromatic region (sm or dba?). 1H NMR (400 MHz, CDCl3) d 1.65 - 2.01 (m, 4H), 2.45 (dtd, 2H), 4.54 (h, 1H), 6.49 (dd, 1H), 7.41 (dd, 1H), 8.01 (dd, 1H). Expected Number of Hs: 11 Assigned Hs: 10, NH not assigned. LC-MS: OK, 86% product. M+1=183 found.

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