Cyclopentanone → 6-Bromo-N-cyclopentylpyridin-3-amine

Participants

Reaction Steps

To a solution of 6-bromopyrid-3-ylamine (2.0 g, 11.6 mmol) in CH2Cl2 (30 mL) was added cyclopentanone (1.3 mL) 15.5 mmol), followed by TiCl4 (1.4 mL, 12.7 mmol) in CH2Cl2 (20 mL) and after stirring for 3.5 h at room temperature, NaBH3CN (2.17 g, 34.5 mmol) was added portion-wise. The reaction was left to stir overnight at ambient temperature, diluted with t-BuOMe (200 mL), washed with water, brine and dried (Na2SO4). Solvent removal and purification by chromatography afforded the sub-title compound (880 mg, 40%).

Provenance & Evidence