Benzoic acid, 2-mercapto-, methyl ester → Methyl 2-{[2-(4-fluorophenyl)quinolin-6-yl]thio}benzoate

Participants

Reaction Steps

A mixture of 6-bromo-2-(4-fluorophenyl)quinoline (Example 19 Step 1; 758 mg, 2.51 mmol), methyl thiosalicylate (0.35 mL, 2.54 mmol), N,N-diisopropylethylamine (0.87 mL, 4.99 mmol), tris(dibenzylideneacetone)dipalladium(0) (58 mg, 0.063 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (74 mg, 0.128 mmol) in 1,4-dioxane (15 mL) was degassed then heated at reflux under nitrogen for 15 hours. The reaction mixture was allowed to cool, concentrated in vacuo and the residue purified by flash chromatography, eluting with 15-25% ethyl acetate/isohexane, to afford methyl 2-{[2-(4-fluorophenyl)quinolin-6-yl]thio}benzoate (0.876, 90%). 1H NMR (400 MHz, CDCl3) δ 8.20-8.14 (4H, m), 8.08 (1H, d, J 1.9 Hz), 8.01 (1H, dd, J 1.6, 7.8 Hz), 7.88 (1H, d, J 8.6 Hz), 7.76 (1H, dd, J 2.0, 8.7 Hz), 7.23-7.15 (4H, m), 6.91 (1H, dd, J 0.9, 8.0 Hz), 3.97 (3H, s); m/z (ES+) 390 [MH+].

Provenance & Evidence