Sodium borohydride → 1-(6-Bromopyridin-3-yl)methanamine

Add dropwise a solution of 2-bromo-pyridine-5-carbaldehyde oxime (0.5 g, 2.487 mmol) in DME (10 mL) to a solution of titanium(IV) chloride (0.573 mL, 5.223 mmol) and sodium borohydride (395 mg, 10.445 mmol) in DME (20 mL) at 0° C. Allow the mixture to warm to room temperature and stir for 3 h. Add water and remove the solvent in vacuo. Basify the mixture to pH 12 with 1N aqueous NaOH and extract with dichloromethane. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to afford the desired intermediate (340 mg, 73%) that was used without further purification.

1. customAdd water and remove the solvent in vacuo
2. extractionBasify the mixture to pH 12 with 1N aqueous NaOH and extract with dichloromethane
3. dry with materialDry the combined organic extracts over Na2SO4
4. filtrationfilter
5. concentrationconcentrate in vacuo

ORD record

ord-11607c0e7eee4bcabdc7c923297baa9d

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022062B2