Ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate → HCID 56597689, compound

Participants

Reaction Conditions

Reaction Steps

Intermediate 16B (0.25 g, 1.13 mmol) was mixed with ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate (0.27 g, 1.25 mmol) in a microwave vial, which then was sealed. The mixture was melted in a preheated oil bath and then stirred at 120° C. for 15 min using the oil bath. EtOH (0.2 mL) was added to the reaction mixture via a syringe and the mixture was stirred at 120° C. for another 3 h. To the mixture was added EtOH (5 mL) and the precipitate was stirred at rt for 20 min. The precipitate was filtered, washed with EtOH (20 mL) and then with Et2O (3 mL). The product was dried in vacuo. There was obtained 0.26 g (57%) of 16 as a solid. 1H NMR (500 MHz, CDCl3): δ 2.23 (s, 6H), 2.35 (s, 3H), 3.32 (s, 2H), 4.29-4.37 (m, 1H), 4.60-4.69 (m, 1H), 4.71-4.79 (m, 1H), 5.02-5.17 (m, 2H), 6.52-6.57 (m, 1H), 6.61 (s, 1H), 7.17 (d, 1H), 7.50-7.62 (m, 3H), 8.17 (d, 2H), MS (APCI+) m/z 393 [M+H]+, LC purity: 98%.

Provenance & Evidence