Toluene → HCID 86751474, compound

Participants

Reaction Steps

To a solution of 11-chloro-6-fluoroquindoline from Example 89 (0.110 g, 3.89 mmol) and toluene (5 ml, freshly distilled) stirring under nitrogen was added methyl triflate (0.110 mL, 0.972 mmol). The mixture stirred for 24 h at room temperature and was diluted with diethyl ether (15 mL) and filtered. The orange filter cake was placed under high vacuum for 24 h. The orange residue was suspended in chloroform (400 mL), 5% KOH (150 mL) was added, and the resulting violet organic solution was separated. The violet organic solution was dried (Na2SO4) and filtered. The violet filtrate was acidified with ethereal 1M HCl to a bright yellow endpoint and adsorbed onto basic alumina. The adsorbent was chromatographed over basic alumina (eluting with chloroform-ethyl acetate gradient from 1:0 to 4:1 until the eluent was free of impurities by TLC then eluting with 2% methanol in chloroform). The violet fractions were collected and concentrated to a small volume (20 mL). The violet solution was acidified with ethereal 1 M HCl to a bright yellow endpoint. The mixture was cooled below room temperature and filtered. The filter cake rinsed with diethyl ether (5 mL) and dried under high vacuum at 45° C. for several days to yield 0.109 g (98%) of the title compound as a bright orange solid. The title compound is poorly soluble in all common NMR solvents; 1H NMR (DMSO-d6 /CD3OD 1:1 v/v) δ 8.64 (d, J=9.2, 1H), 8.63 (dd, J=8.0, J=1.2, 1H), 8.18 (ddd, J=9.2, J=6.6, J=1.2, 1H), 8.00 (ddd, J=8.4, J=6.2, J=1.2, 1H), 7.87 (td, J=8.4, J=5.2, 1H), 7.59 (dd, J=8.4, J=0.4, 1H), 7.22 (ddd, J=13.6, J=8.0, J=0.8, 1H), 4.98 (s, 3H).

Provenance & Evidence