2-(Pyridin-2-yl)but-3-yn-2-ol → (+/-)-9-fluoro-10-(3-hydroxy-3-(pyridin-2-yl)but-1-yn-1-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide

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Reaction Steps

9-fluoro-10-(3-hydroxy-3-(pyridin-2-yl)but-1-yn-1-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide was prepared similarly according to General Procedure G with slight modifications. 10-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide was reacted with 2-(2-pyridyl)but-3-yn-2-ol to afford 7.5 mg of the titled compound (6.3% yield). M+1=403.1. 1H NMR (400 MHz, DMSO) δ 8.64 (d, J=7.6 Hz, 1H), 8.58 (d, J=4.6 Hz, 1H), 7.90-7.84 (m, 1H), 7.82 (s, 1H), 737 (d, J=7.9 Hz, 1H), 7.57 (br s, 1H), 7.38-7.32 (m, 1H), 7.29 (d, J=10.1 Hz, 1H), 7.11 (br s, 1H), 6.47 (s, 1H), 4.94-4.87 (m, 1H), 3.75-3.67 (m, 1H), 3.14-3.03 (m, 2H), 1.83 (s, 3H), 1.71-1.64 (m, 2H).

Provenance & Evidence