Water → 6-Bromo-3-(4-fluorophenyl)-imidazo[1,2-a]pyridine

To a mixture of commercially available 6-bromo-3-iodoimidazo[1,2-a]pyridine (0.7 g, 2.17 mmol) and commercially available 4-fluoro-phenylboronic acid (0.3 g, 2.17 mmol) in 1,2-dimethoxyethane (14 ml), 2M sodium carbonate solution (2.71 ml, 5.42 mmol) was added, and the reaction mixture was purged with argon for 5 min in an ultrasonic bath. Afterwards tetrakis(triphenylphosphine)palladium(0) (125 mg, 108 μmol) was added, and the stirred reaction mixture was heated under reflux conditions for 17 h. The reaction mixture was cooled to room temperature, poured into water (30 ml) and extracted with ethyl acetate (2×40 ml). The combined organic layers were washed with brine (30 ml), dried (MgSO4) and evaporated. The crude material (0.74 g) was further purified by flash chromatography on silica gel (dichloromethane/MeOH 98:2) and trituration (diethyl ether) to yield the title compound as a light yellow solid (0.3 g, 48%), MS (ISP) m/z=291.3 [(M+H)+], mp 102° C.

1. additionwas added
2. customthe reaction mixture was purged with argon for 5 min in an ultrasonic bath
3. customthe stirred reaction mixture
4. temperaturewas heated under reflux conditions for 17 h
5. extractionextracted with ethyl acetate (2×40 ml)
6. washThe combined organic layers were washed with brine (30 ml)
7. dry with materialdried (MgSO4)
8. customevaporated
9. customThe crude material (0.74 g) was further purified by flash chromatography on silica gel (dichloromethane/MeOH 98:2) and trituration (diethyl ether)

ORD record

ord-9291e0b5f4c94a37a126c240e8fd7a8d

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315502B2