反应详情

Methyl 3-methoxy-4-(5-nitroindol-3-ylmethyl)benzoate (F) (5.30 g) was added to a stirred suspension of oil-free sodium hydride (0.424 g) in dry N,N-dimethylformamide (25 ml), under an atmosphere of nitrogen. The dark-red solution was stirred for 15 minutes, and iodoethane (3.04 g) was added. The mixture was stirred for 30 minutes, and was poured into 1M hydrochloric acid (75 ml). The mixture obtained was extracted wih ethyl acetate (2×50 ml). The combined extracts were washed with brine (25 ml), then dried (MgSO4), and evaporated. The yellow oil obtained was purified by flash chromatography on silica gel (600 ml), eluting with 70:30 v/v hexane:ethyl acetate, to give methyl 3-methoxy-4-(1-ethyl-5-nitroindol-3-ylmethyl)benzoate (G) as a yellow oil, which was crystallized from methylene chloride/hexane to give yellow needles (4.88 g, 82%); mp 129°-30° C.; 1.34(t, 3H, CH2CH3), 3.83(s, 3H, CO.OCH3), 3.92(s, 3H, OCH3), 4.11 (s, 2H, CH2Ar), 4.23(q, 2H, CH2CH3), 7.27(d, 1H), 7.48(m, 2H), 7.64(d, 1H), 7.99(dd, 1H, H6 -indole), 8.49(d, 1H, H4 -indole).

1. stirringThe mixture was stirred for 30 minutes
2. customThe mixture obtained
3. extractionwas extracted wih ethyl acetate (2×50 ml)
4. washThe combined extracts were washed with brine (25 ml)
5. dry with materialdried (MgSO4)
6. customevaporated
7. customThe yellow oil obtained
8. customwas purified by flash chromatography on silica gel (600 ml)
9. washeluting with 70:30 v/v hexane