Chloroacetaldehyde → 5-Bromo-8-methylimidazo[1,2-a]pyridine

Temperature

100 °C

A mixture of 6-bromo-3-methylpyridin-2-ylamine (359 mg, 1.92 mmol) and chloroacetaldehyde (1 mL, 50 wt. % in water) in IMS (4 mL) was stirred at 100° C. in a sealed tube for 1.5 hours, then cooled to room temperature and loaded onto an Isolute® SCX-2 cartridge (10 g). The cartridge was washed with MeOH then eluted with 2 M NH3 in MeOH to give 5-Bromo-8-methylimidazo[1,2-a]pyridine as a beige solid (387 mg, 95%). 1H NMR (400 MHz, CHCl3-d): δ 7.79 (d, J=1.3 Hz, 1 H); 7.69 (d, J=1.3 Hz, 1 H); 6.96 (d, J=7.3 Hz, 1 H); 6.91 (dq, J=7.3, 1.1 Hz, 1 H); 2.61 (d, J=1.1 Hz, 3 H).

1. temperaturecooled to room temperature
2. washThe cartridge was washed with MeOH
3. washthen eluted with 2 M NH3 in MeOH

ORD record

ord-e1725fbf5ede41ce9ec2d693abeb259e

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394796B2