反应详情

A mixture of 1-(1-isocyanopropylsulfonyl)-4-methylbenzene (1.98 g, 8.87 mmol), 5-bromopicolinaldehyde (1.65 g, 8.87 mmol), and K2CO3 (1.47 g, 10.6 mmol) in MeOH (45 mL) was heated at reflux overnight. The reaction was cooled to ambient temperature and concentrated in vacuo. Water was added to the residue and the product was extracted with EtOAc. The combined organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was chromatographed on silica gel (Analogix® 25×60 column, 10%-50% EtOAc/hexanes) to yield 1.97 g (88%) of the title compound. 1H NMR (300 MHz, CDCl3) δ 8.68 (dd, J=2.4, 0.5, 1H), 7.89-7.82 (m, 2H), 7.55-7.49 (m, 1H), 3.06 (q, J=7.5, 2H), 1.29 (t, J=7.5, 3H). MS (DCI+) m/z 253/255 (M+H).

1. temperaturewas heated
2. temperatureat reflux overnight
3. concentrationconcentrated in vacuo
4. additionWater was added to the residue
5. extractionthe product was extracted with EtOAc
6. extractionThe combined organic extract
7. washwas washed with brine
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe crude product was chromatographed on silica gel (Analogix® 25×60 column, 10%-50% EtOAc/hexanes)