3-Oxetanone → methyl 10-bromo-9-fluoro-3-(3-hydroxyoxetan-3-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate

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Reaction Steps

Methyl 10-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate (0.3 g) was reacted with oxetan-3-one similar to as described in example 8 with non-critical modifications to produce methyl 10-bromo-9-fluoro-3-(3-hydroxyoxetan-3-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate. This crude intermediate was reacted via General Procedure L to provide 10-bromo-9-fluoro-3-(3-hydroxyoxetan-3-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide which was reacted as a crude with 2-Methyl-3-butyne-ol via General Procedure F to afford 23 mg (51.1%) 9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-3-(3-hydroxyoxetan-3-yl)-5,6,7,12-tetrahydro-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide.

Provenance & Evidence