7-[2-(1H-indol-5-yloxy)-ethyl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester → HCID 66821111, compound

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Reaction Steps

The title compound was synthesized from 3-chloro-3-p-tolyl-acrylic acid ethyl ester and 7-[2-(1H-indol-5-yloxy)-ethyl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester using the procedure outlined in Example 18, step (d), in a 36% yield of E/Z isomeric mixture. 1H NMR (CDCl3) [E/Z mixture] δ 7.33 (m, 1.4H), 7.17 (m, 4.6H), 6.96 (m, 1.6H), 6.74 (m, 2.4H), 6.57 (d, 0.8H, J=0.8 Hz), 6.50 (d, 0.2H, J=0.8 Hz), 6.20 (s, 0.8H), 6.11 (s, 0.2H), 4.39 (t, 2H, J=8.0), 4.01 (m, 2H), 3.78 (t, 2H, J=4.0), 3.22 (t, 2H, J=8.0), 2.75 (t, 2H, J=8.0), 2.44 (s, 0.6H), 2.40 (s, 2.4H), 1.94 (m, 2H), 1.53 (s, 9H), 1.05 (t, 3H, J=8.0 Hz).

Provenance & Evidence