Reaction Steps
To a hot solution of the bisamide 21b (0.58 g, 1.00 mmol) in ethanol (10 mL) was added 10% sodium hydroxide (10 mL), and the whole was heated at reflux for 40 min. The reaction mixture was then evaporated to dryness under reduced pressure, water was added and the solid was filtered and washed with water to give 20v as a gold solid (0.42 g, 90%), mp 105-107° C. (from acetonitrile). 1H NMR (CDCl3): δ 2.31 [s, 6H, N(CH3)2], 2.64 (t, J=6.4 Hz, 2H, CH2CH2NMe2), 2.82 (s, 3H, ArCH3), 3.21 (t, J=7.7 Hz, 2H, CH2CH2Indole), 3.73 (q, J=6.1 Hz, 2H, CH2CH2NMe2), 4.30 (t, J=7.8 Hz, 2H, CH2CH2Indole), 6.99 (d, J=2.0 Hz, 1H, H-2′), 7.06-7.14 (m, 2H, H-5′, H-6′), 7.30 (d, J=7.7 Hz, 1H, H-7′), 7.46 (t, J=7.6 Hz, 1H, H-8), 7.66-7.70 (m, 2H, H-4′, H-7), 7.82 (d, J=8.2 Hz, 1H, H-9), 8.51 (s, 1H, H-3), 8.62 (s, 1H, H-1′), 9.24 (s, 1H, H-10), 10.98 (br t, J=5.3 Hz, 1H, CONH). 13C NMR (CDCl3): δ 18.2 (ArCH3), 24.8 (CH2CH2Indole), 37.2 (CH2CH2NMe2), 45.0 [N(CH3)2], 50.2 (CH2CH2Indole), 58.4 (CH2CH2NMe2), 109.0 (C), 110.9 (CH, C-7′), 111.1 (C), 118.2 (CH, C-4′), 119.2 (CH, C-5′), 121.7 (CH, C-6′), 122.0 (CH, C-2′), 125.6 (C-9a), 126.2 (CH, C-8), 126.8 (C-3a′), 127.0 (CH, C-9), 132.5 (CH, C-7), 135.5 (C-6), 136.0 (C-7a′), 139.5 (CH, C-3), 142.7 (CH, C-10), 147.8 (C-5a), 148.4 (C-4a), 162.1 (C-1), 164.4 (CONH). Indole C-3′ was not observed.
