反应详情

Sodium hydride (0.15 g of a 60% dispersion in mineral oil) was added to a stirred solution of E,E-3,6-di(3-oxo-3-pyrrolidino-1-propenyl)indole (0.97 g) in N,N-dimethylformamide (30 ml) cooled in an ice bath. After approximately 1 hr a solution of methyl-4-bromomethyl-3-methoxybenzoate (0.74 g) in N,N-dimethylformamide (10 ml) was added dropwise, the cooling bath was removed, and the mixture stirred for hr. The mixture was added slowly to vigorously stirred 1M hydrochloric acid (300 ml); the precipitate was isolated by filtration, washed with water and dried. The solid obtained was recrystallized from ethyl acetate to give methyl E,E-4-[3,6-di(3-oxo-3-pyrrolidino-1-propenyl)indol-1-ylmethyl]-3-methoxybenzoate (1.1 g, 76%) as an off-white powder; mp 226°-228°; partial NMR (250 MHz, DMSO-d6): 1.70°-2.0(m, 8H, pyrrolidino H), 3.40(m, 4H, pyrrolidino H), 3.65(m, 4H, pyrrolidino H), 3.83(s, 3H, OCH3), 3.95(s, 3H, OCH3), 5.50(s, 2H, NCH2Ar), 6.75(d, J=15.5 Hz, 1H, olefinic H), 7.0(m, 2H, olefinic H, and ArH).

1. temperaturecooled in an ice bath
2. customthe cooling bath was removed
3. additionThe mixture was added slowly to vigorously stirred 1M hydrochloric acid (300 ml)
4. customthe precipitate was isolated by filtration
5. washwashed with water
6. customdried
7. customThe solid obtained
8. customwas recrystallized from ethyl acetate