Ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate → 4-{4-[(1-{[5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl]carbonyl}azetidin-3-yl)oxy]-3-methylbenzyl}morpholine

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Reaction Conditions

Reaction Steps

A mixture of 12B (0.18 g, 0.69 mmol) and ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate (0.19 g, 0.75 mmol) was heated to 120° C. for 3 h using an oil-bath. Ethanol (0.1 mL) was added and the mixture was further heated to 120° C. for 30 min. The product was purified by column chromatography eluting with DCM and then with MeOH/DCM (0.5-2%). There was obtained 0.23 g (71%) of 12 as a solid. 1H NMR (600 MHz, CDCl3): δ 2.22 (s, 3H), 2.33-2.50 (m, 4H), 3.39 (s, 2H) 3.60-3.77 (m, 4H), 3.86 (s, 3H), 4.26-4.36 (m, 1H), 4.57-4.78 (m, 2H), 4.99-5.16 (m, 2H), 6.42 (d, 1H), 6.99 (d, 2H), 7.05 (d, 1H), 7.12 (s, 1H), 8.07 (d, 2H), MS (APCI+) m/z 465 [M+H]+, LC purity: 99%.

Provenance & Evidence