Bromine → HCID 67485364, compound

Participants

Reaction Steps

3-(cyclopentyloxy)-2-nitropyridine (8.2 g, 39.3 mmol) in acetic acid (90 mL) was cooled in a water bath. Zn dust (10 microns) (12.9 g, 197 mmol) was slowly added in portions over 15 minutes and the reaction stirred for an additional 30 minutes. The solution was filtered over celite and the solids were rinsed with DCM. The filtrate was concentrated to about 90 mL of acetic acid. To this solution was added bromine (2.0 mL, 39.3 mmol) in dropwise manner. After 15 minutes, the material was concentrated and neutralized with saturated NaHCO3 solution. The material was extracted with dichloromethane and the organic layer was dried, and concentrated. Flash chromatography gave 5-bromo-3-(cyclopentyloxy)pyridin-2-amine (5.26 g, 52% yield) as a yellow solid.

Provenance & Evidence