Toluene → HCID 42643906, compound

Participants

Reaction Steps

To N-[3-(8-Amino-imidazo[1,2-a]pyridin-6-yl)-2-methyl-phenyl]-4-tert-butyl-benzamide (53 mg, 0.133 mmol) in dichloromethane (5 mL) at 0° C. was added diisopropylethylamine (60 μL, 2.5 eq) and the resulting mixture was stirred for 5 minutes. Then at 0° C. with stirring was added a 20% phosgene solution in toluene (84 μL, 1.2 eq) all at once, and the resulting solution was stirred at 0° C. for 5 minutes. Next, ethylamine(g) was bubbled through the solution for about 2 minutes. Additional phosgene solution (0.25 mL) was added at 0° C. and stirred an additional 5 minutes. Finally, ethylamine(g) was bubbled through the solution again for about 2 minutes. The reaction was quenched by adding ethyl acetate (35 mL) and water (25 mL). The layers were partitioned and then separated and the organic layer was further washed with brine (1×25 mL) and finally dried over magnesium sulfate, filtered and concentrated. This crude product was purified by Preparative Thin Layer Chromatography, eluting with 5% methanol in dichloromethane to give the title compound as a foamy solid (17 mg) ((M+H)+=470).

Provenance & Evidence