反应详情

温度

125 °C

A mixture of 6-(4-fluorophenyl)-2-naphthyl trifluoromethanesulfonate (Ex 1 Step 2, 150 mg, 0.41 mmol), 1-methyl-1H-imidazole-2-thiol (47 mg, 0.41 mmol), tris(dibenzylideneacetone)dipalladium(0) (16 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (20 mg) and diisopropylethylamine (0.15 mL, 0.82 mmol) in dioxane (3 mL) was heated to 125° C. under nitrogen for 15 h. The cooled reaction mixture was poured into water and extracted with ethyl acetate (x3). The combined organic layers were washed with water and brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 25% ethyl acetate/isohexane, to give the title compound as an oil (125 mg). 1H NMR (500 MHz, CDCl3): δ 7.90 (1H, s), 7.75 (2H, t, J=8.6 Hz), 7.66-7.59 (4H, m), 7.27 (2H, m), 7.15 (2H, m), 7.10 (1H, s), 3.65 (3H, s); m/z (ES+) 335 [MH+].

1. customThe cooled reaction mixture
2. extractionextracted with ethyl acetate (x3)
3. washThe combined organic layers were washed with water and brine
4. dry with materialdried (MgSO4)
5. customevaporated in vacuo
6. customThe residue was purified by flash column chromatography on silica
7. washeluting with 25% ethyl acetate/isohexane