Hydrochloric Acid → HCID 9799764, compound

Participants

Reaction Steps

A solution of 2,3-dihydro-1H-pyrano[3,2-f]quinolin-2-amine (intermediate 1a) (0.68 g, 3.4 mmol), 3-(3-bromopropyl)-5-fluoro-1H-indole (0.58 g, 2.26 mmol), and triethylamine (0.63 mL, 4.52 mmol) in anhydrous dimethylsulfoxide (40 mL) was stirred at 80° C. for 12 hrs. The reaction mixture was poured into ice-H2O and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. Chromatography (5% MeOH/CH2Cl2) afforded 0.54 g (64%) of product as a brown oil. It was converted to the HCl salt by dissolution in ethyl acetate and addition of 1M HCl/Et2O solution (2.4 eq) to generate N-[3-(5-fluoro-1H-indol-3-yl)propyl]-2,3-dihydro-1H-pyrano[3,2-f]quinolin-2-amine bis-hydrochloride salt as a light brown solid: mp>180° C. MS ESI m/z 376 [M+H]+. Elemental Analysis for C23H22FN3O·2.00 HCl·0.25 H2O; Calculated: C, 61.00; H, 5.45; N, 9.28. Found: C, 61.02; H, 5.66; N, 9.03.

Provenance & Evidence