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. 2014 Apr 28;57(10):4173–4184. doi: 10.1021/jm5000672

Scheme 1. Synthesis of First Generation 1-Indole Cinnamic Amide EP2 Antagonists.

Scheme 1

Reagents and conditions: (a) NaH, bromoacetonitrile, DMF, 75%; (b) lithium aluminum hydride (LAH), tetrahydrofuran (THF), 32–57%; (c) cinnamic acid drivative (4), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI), dimethylaminopyridine (DMAP), CH2Cl2, 75–80%.