Reaction #2032778

Reaction equation

6-bromo-5-fluoropyridin-2-ylamine

chloroacetaldehyde

→

5-Bromo-6-fluoroimidazo[1,2-a]pyridine

Yield 89.0%

Solvents

Conditions

Workup

1. 1
   Temperaturecooled to room temperature
2. 2
   WashThe desired product was washed with MeOH
3. 3
   Washthen eluted with 2 M NH3 in MeOH

Procedure

A mixture of 6-bromo-5-fluoropyridin-2-ylamine (25 mg, 0.13 mmol) and chloroacetaldehyde (0.1 mL, 50 wt. % in water) in IMS (2 mL) was stirred at 100° C. in a sealed tube for 18 hours, then cooled to room temperature and loaded onto an Isolute® SCX-2 cartridge (5 g). The desired product was washed with MeOH then eluted with 2 M NH3 in MeOH to give 5-Bromo-6-fluoroimidazo[1,2-a]pyridine as a yellow oil (25 mg, 89%). 1H NMR (400 MHz, CHCl3-d): δ 7.84 (s, 1 H); 7.76 (m, 1 H); 7.61 (ddd, J=9.73, 4.67, 0.71 Hz, 1 H); 7.21-7.16 (m, 1 H).

Source