Sodium Azide → (5-Fluoropyridin-2-yl)methanamine

Dissolve methanesulfonic acid (5-fluoro-pyridin-2-yl)-methyl ester (1.5 g, 7.3 mmol) in DMF (5 mL) and add sodium azide (950 mg, 14.6 mmol). Stir the mixture for 30 min, then dilute with hexane/EtOAc (1:1, 50 mL). Wash the mixture with 10% aqueous NaCl (3×10 mL). Dry the combined organic extracts over Na2SO4 and remove half of the solvent in vacuo. Add EtOAc (20 mL) and a suspension of 10% Pd/C (200 mg) in EtOAc (2 mL). Stir the mixture for 1 h at ambient temperature in a pressurized vessel under 50 psi of hydrogen. Filter the slurry through Celite® and concentrate in vacuo to obtain 2-aminomethyl-5-fluoro-pyridine (613 mg, 60% yield, 80% purity by GC/MS). GC-MS m/z: 126 (M+).

1. washWash the mixture with 10% aqueous NaCl (3×10 mL)
2. dry with materialDry the combined organic extracts over Na2SO4
3. customremove half of the solvent in vacuo
4. additionAdd EtOAc (20 mL) and a suspension of 10% Pd/C (200 mg) in EtOAc (2 mL)
5. stirringStir the mixture for 1 h at ambient temperature in a pressurized vessel under 50 psi of hydrogen
6. filtrationFilter the slurry through Celite®
7. concentrationconcentrate in vacuo

ORD record

ord-ddee198899f84b3aa7913a68fa9d31fe

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022062B2