反应详情

A stirred solution of methyl 4-(5-aminoindol-3-ylmethyl)-3-methoxybenzoate (A) (0.2 g.) in dichloromethane (5 ml.) under an atmosphere of nitrogen, was treated with N-methylmorpholine (0.25 g.), followed by hexanoyl chloride (0.103 g.). After being stirred for 2 hours, the mixture was poured into 1M hydrochloric acid (20 ml.). This mixture was extracted with ethyl acetate (2x20 ml.). The combined organic extracts were dried (MgSO4) and evaporated. The yellow oil obtained was purified by flash chromatography on silica gel (75 ml.), eluting with 6:4 v/v ethyl acetate:hexane, to give the title compound (0.24 g., 92%) as a colorless oil: NMR: 0.83 (t,3 H, CH2.CH3), 1.36 (m,4 H, CH2.CH2.CH3), 1.57 (quintet,2 H, CH2.CH2CON), 2.24 (t, 2 H, CH2.CON), 3.80 (s,3 H, COOCH3), 3.90 (s,3 H, OCH3), 3.99 (s,2 H, CH2.Ar), 7.1 (m, 2 H), 7.21 (m,2 H), 7.44 (m,2 H), 7.69 (s,1 H,H4 -indole), 9.59 (s,1 H, CONH), 10.77 (s,1 H, H1 -indole).

1. extractionThis mixture was extracted with ethyl acetate (2x20 ml.)
2. dry with materialThe combined organic extracts were dried (MgSO4)
3. customevaporated
4. customThe yellow oil obtained
5. customwas purified by flash chromatography on silica gel (75 ml.)
6. washeluting with 6:4 v/v ethyl acetate