Dichloromethane → 8-[4-(3,4-Dimethoxy-phenyl)-pyrrolo[2,3-b]pyridine-1-sulfonyl]-quinoline

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Reaction Steps

Into a Round bottom flask was added 4-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine (0.222 g, 0.000873 mol), 50 and Tetra-N-butylammonium bromide (0.0282 g, 0.0000874 mol), and 5.000 M of Sodium hydroxide in Water (2.25 mL). 8-quinoline-sulfonyl chloride (0.238 g, 0.00105 mol) dissolved in Methylene chloride (0.616 mL, 0.00960 mol) was added dropwise at 0 Celsius. The reaction was stirred at ambient temperature for 3 h and the reaction mixture was diliuted with an addional 25 mL of methylene chloride. The organic layer was washed with 1 M sodium bicarbonate (aq.) (30 ml×2) and then with brine. The separated organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (30% ethyl acetate in hexanes) to yield the titled compound as a white solid. MS(ESI) [M+H+]+=446.20.

Provenance & Evidence