Sodium hydride → HCID 19870592, compound

Participants

Reaction Steps

Sodium hydride (0.12 g of a 60% dispersion in mineral oil) was added to a stirred solution of E-N-propylindole-6-acrylamide (0.7 g) in N,N-dimethylformamide (35 ml) cooled by an ice bath. After approximately 1 hr, a solution of methyl 4-bromomethyl-3-methoxybenzoate (0.79 g) (see Example 1, part 1) in N,N-dimethylformamide (2 ml) was added, the cooling bath removed and the mixture stirred for 1 hr. The mixture was poured into ice and extracted with ethyl acetate. The extracts were washed with brine, dried (MgSO4) and evaporated. The residue was crystallized from a mixture of ethyl acetate and hexane to give methyl E-4-[6-[2-(propylcarbamoyl)vinyl]indol-1-ylmethyl]-3-methoxybenzoate (0.78 g) as a white solid. The mother liquor was evaporated and the residue was purified by flash chromatography, eluting with 1:1 ethyl acetate:hexane, to give a further quantity of the product (0.23 g, 84% combined yield); partial NMR (250 MHz, DMSO-d6): 0.87(t, 3H, CH2CH2CH3), 1.45(m, 2H, CH2CH2CH3), 3.12(m, 2H, CH2CH2CH3) 3.83(s, 3H, OCH3), 3.96(s, 3H, OCH3), 5.46(s, 2H, NCH2Ar), 7.98(br t, 1H, NHCO).

Provenance & Evidence