Methyl triflate → HCID 86751475, compound

Participants

Reaction Steps

To a solution of 11-chloro-8-fluoroquindoline from Example 89 (1.00 g, 3.69 mmol) in toluene (25 ml, freshly distilled) stirring under nitrogen was added methyl triflate (1.05 mL, 9.24 mmol). The mixture stirred for 24 h at room temperature and was diluted with diethyl ether (60 mL) and filtered. The orange filter cake was placed under high vacuum for 24 h. The orange residue was suspended in chloroform and adsorbed onto neutral alumina and chromatographed over basic alumina (eluting with chloroform-ethyl acetate gradient from 1:0 to 1:1 until the eluent was free of impurities by TLC then eluting with 3% methanol in chloroform). The violet fractions were collected and concentrated to a small volume (50 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 (10 mL) and dried under high vacuum at 45° C. for several days to yield 0.949 g (90%) of the title compound as a bright orange solid. A portion of this material was further purified by HPLC. The title compound is poorly soluble in all common NMR solvents; 1H NMR (DMSO-d6) δ 13.55 (s, 1H), 8.93 (dd, J=9.0, J=5.2, 1H), 8.87 (d, J=8.8, 1H), 8.68 (d, J=8.0, 1H), 8.27 (t, J=8.0, 1H), 8.11 (t, J=7.6, 1H), 7.64 (dd, J=9.0, J=2.2, 1H), 7.47 (J=9.2, J=2.2, 1H), 5.00 (s, 3H); MS (FAB, m/z) 285 (M+).

Provenance & Evidence