反应详情

EDAC (0.500 g, 2.6 mmol) was added to a solution of 2-aminodibenzothiophene (0.470 g, 2.4 mmol), 1-hydroxybenzotriazole (0.351 g, 2.6 mmol) and 3-methyl-3-pyridin-4-ylpropanoic acid (Method 7; 0.429 g, 2.6 mmol) in DMF (10 ml). The solution was then stirred at room temperature overnight. The solvent was removed in vacuo and the residue was then shaken in water (50 ml) and DCM (50 ml). The organic layer was separated, washed with brine (50 ml), dried and then evaporated in vacuo to leave a light brown solid. The crude amide was dissolved in a mixture of glacial acetic acid (15 ml) and concentrated sulphuric acid (0.5 ml) at 60° C. and hydrogen peroxide (30 wt. % solution in water, 3 ml) was added. The mixture was stirred at 60° C. for 2 hours and left to cool to room temperature overnight. The mixture was poured into water (50 ml) and made basic by the addition of potassium carbonate. The mixture was extracted into DCM (50 ml), the organic layer was separated and washed with brine (50 ml), dried and evaporated in vacuo to leave a light brown solid. The crude product was triturated with methanol (10 ml) to leave a pale yellow solid (0.496 g). NMR: 10.47 (s, 1H), 8.3 (d, 1H), 7.9 (m, 3H), 7.75 (t, 1H), 7.65 (m, 2H), 3.3 (m, 1H), 2.7 (m, 2H), 1.3 (d, 3H); m/z 379.

1. customThe solvent was removed in vacuo
2. stirringthe residue was then shaken in water (50 ml)
3. customThe organic layer was separated
4. washwashed with brine (50 ml)
5. customdried
6. customevaporated in vacuo
7. customto leave a light brown solid
8. stirringThe mixture was stirred at 60° C. for 2 hours
9. waitleft
10. temperatureto cool to room temperature overnight
11. extractionThe mixture was extracted into DCM (50 ml)
12. customthe organic layer was separated
13. washwashed with brine (50 ml)
14. customdried
15. customevaporated in vacuo
16. customto leave a light brown solid
17. customThe crude product was triturated with methanol (10 ml)