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0 °C

4-tert-Butyl-o-anisidine (54 mg, 0.301 mmol, 1 equiv.) was dissolved in 15 mL dichloromethane and 15 mL of saturated aqueous NaHCO3 solution was added. The biphasic mixture was cooled to 0° C. and phosgene (˜2 M solution in toluene, 0.75 mL) was added to the organic layer via syringe in one portion, without stirring. The mixture was then stirred vigorously for 10 min, then the layers were separated. The aqueous layer was extracted once with dichloromethane and the combined organics were dried (Na2SO4), filtered and most of the dichloromethane was removed in vacuo, leaving the toluene. To this isocyanate residue was then added 1-(4-aminonaphthalen-1-yl)pyrrolo[3,2-c]pyridine (Example 1) (77 mg, 0.297 mmol, 1 equiv.) dissolved in 5 mL anhydrous THF. The mixture was left to stir at room temperature for 2 h, then the solvents were removed in vacuo. The residue was purified by column chromatography on SiO2 using dichloromethane/MeOH eluent mixtures. The isolated enriched fraction was further purified by reverse-phase preparative HPLC to provide 20 mg of the title compound as a white foam.

1. stirringThe mixture was then stirred vigorously for 10 min
2. customthe layers were separated
3. extractionThe aqueous layer was extracted once with dichloromethane
4. dry with materialthe combined organics were dried (Na2SO4)
5. filtrationfiltered and most of the dichloromethane
6. customwas removed in vacuo
7. customleaving the toluene
8. waitThe mixture was left
9. stirringto stir at room temperature for 2 h
10. customthe solvents were removed in vacuo
11. customThe residue was purified by column chromatography on SiO2
12. customThe isolated enriched fraction was further purified by reverse-phase preparative HPLC