Water → 2-Amino-3-phenyl-6-(2-fluorobenzoyl)-imidazo[1,2-a]pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-bromo-2-fluorobenzene (191 mL, 1.75mmol) in dry THF (2 mL) under an argon atmosphere was added t-butyl lithium dropwise. After stirring for 50 minutes at −78° C., a solution of 2-amino-3-phenyl-6-(N-methyl-N-methoxycarbamoyl)imidazo[1,2-a]pyridine (148 mg, 0.5 mmol) in dry THF (3 mL) was added. The resulting red-orange solution was stirred at the same temperature for another 50 minutes and then allowed to warm to RT. The solution was poured into H2O (20 mL) and extracted with EtOAc (2×20 mL). The organic layer was washed with H2O, dried (Na2SO4), and removed in vacuo to give a brown solid. The crude solid was purified by column chromatography (CH2Cl2/CH3CN 2.5/1) to give 84.0 mg (50.6%) of product as a yellow solid. MS(FAB) m/z 332.2 (M++1, 51.99), NMR (200 MHz, CDCl3) d 4.27 (bs, 2H, NH), 7.12-7.58 (m, 11H, ArH+H7+H8), 8.71 (s, H5).

Provenance & Evidence