反应详情

温度

90 °C

To a solution of 4-cyclohexyl-5-(3-dimethylamino-2-methyl-acryloyl)-2-methylsulfanyl-thiophene-3-carbonitrile (0.5 g, 1.7 mmol) in toluene (3 ml) was added DMF-DMA and the reaction was heated at 90° C. overnight resulting in conversion to product as determined by TLC (40% EtOAc:hexanes). The crude product was combined with DMF (10 ml) and 3-nitrophenylguanidine (0.5 g, 2.78 mmol) in a sealed tube and heated at 120° C. overnight resulting in conversion to product as determined by TLC (40% EtOAc:hexanes). The reaction was partitioned between EtOAc and water, the organics were dried over sodium sulfate then concentrated in vacuo. The crude product was purified by chromatography (silica gel, 10% EtOAC:hexanes) to afford 0.334 g (3.05 umol) of V-7 in 42% yield for 2 steps. 1H NMR (CDCl3) δ 1.0–2.0 (m, 10H), 2.1 (s, 3H), 2.6 (s, 3H), 7.4 (m, 1H), 7.7 (d, 1H), 7.8 (d, 1H), 8.3 (s, 1H), 8.7 (s, 1H).

1. customresulting in conversion to product
2. temperatureheated at 120° C. overnight
3. customresulting in conversion to product
4. customThe reaction was partitioned between EtOAc and water
5. dry with materialthe organics were dried over sodium sulfate
6. concentrationthen concentrated in vacuo
7. customThe crude product was purified by chromatography (silica gel, 10% EtOAC:hexanes)
8. customto afford 0.334 g (3.05 umol) of V-7 in 42% yield for 2 steps