Ethyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate → 2-(4-Chlorophenyl)-5-({3-[4-(pyrrolidin-1-ylmethyl)phenoxy]azetidin-1-yl}carbonyl)-1,3,4-oxadiazole

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Reaction Conditions

Reaction Steps

A mixture of 1B (1.0 g, 4.3 mmol) and ethyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate—see e.g. WO97/05131—(1.2 g, 4.7 mmol) was heated at 120° C. for 4 h. The residue was purified by column chromatography on SiO2 using 5% triethylamine in EtOAc as eluent. There was obtained 0.46 g (24%) of 1 as a solid. 1H NMR (500 MHz, CDCl3): δ 1.69-1.88 (m, 4H), 2.38-2.69 (m, 4H), 3.57 (s, 2H), 4.26-4.38 (m, 1H), 4.61-4.68 (m, 1H), 4.72-4.79 (m, 1H), 5.05-5.20 (m, 2H), 6.74 (d, 2H), 7.29 (d, 2H), 7.52 (d, 2H), 8.10 (d, 2H), MS (APCI+) m/z 439 [M+H]+, LC purity: 96%.

Provenance & Evidence