N-bromobutanimide → 5-Bromo-6-ethylpyridin-2-amine

Temperature

0 °C

2-Amino-6-ethylpyridine (3.0 g, 24.6 mmol) was dissolved in chloroform (25 mL) and cooled to 0° C. NBS (4.4 g, 24.6 mmol) was added portion-wise over 30 min and the mixture was stirred for 30 min at 0° C. The solvent was removed in vacuo and the residue was slurried with EtOAc (8 mL). The resultant solids were removed by filtration through a pad of diatomaceous earth and filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography (EtOAc/hexanes) to afford 5-bromo-6-ethylpyridin-2-amine (3.83 g, 78%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.42 (d, J=8.6 Hz, 1H), 6.20 (d, J=8.7 Hz, 1H), 6.03 (s, 2H), 2.60 (q, J=7.5 Hz, 2H), 1.10 (t, J=7.5 Hz, 3H); MS (ESI) m/z: 201.0/203.0 (M+H+).

1. customThe solvent was removed in vacuo
2. customThe resultant solids were removed by filtration through a pad of diatomaceous earth and filtrate
3. concentrationwas concentrated in vacuo
4. customThe residue was purified by silica gel chromatography (EtOAc/hexanes)

ORD record

ord-76299325b85749b7ac5e575f5db4de80

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193719B2