反应详情

温度

110 °C

To a solution of 1H-spiro[2-benzopyran-4,1′-cyclopropan]-5-ol (Intermediate 136, 150 mg) in dry N,N-dimethylformamide (4 ml) potassium carbonate (176 mg, 1.277 mmol) and then 2-chloro-5-nitropyridine (148 mg, 0.936 mmol) were added and the reaction mixture was stirred for 1 h at 110° C. After cooling the reaction was quenched with brine (1 ml), diluted with water (5 ml) and extracted with ethyl acetate (3×15 ml). The organic layer was washed with ice cold brine (2×10 ml), dried over sodium sulphate, filtered and evaporated and the residue was purified by flash chromatography (Biotage system) on silica gel using a 25 g SNAP column and cyclohexane/ethyl acetate as eluents from 100:0 to 7:3. This afforded the title compound as a colourless gum (240 mg).

1. temperatureAfter cooling the reaction
2. customwas quenched with brine (1 ml)
3. additiondiluted with water (5 ml)
4. extractionextracted with ethyl acetate (3×15 ml)
5. washThe organic layer was washed with ice cold brine (2×10 ml)
6. dry with materialdried over sodium sulphate
7. filtrationfiltered
8. customevaporated
9. customthe residue was purified by flash chromatography (Biotage system) on silica gel using a 25 g SNAP column and cyclohexane/ethyl acetate as eluents from 100:0 to 7:3