Veratric Acid → ethyl 3-(7-{5-[3,4-bis(methyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-3-yl)propanoate

Beteiligte Stoffe

Reaktionsschritte

To a solution of 3,4-bis(methyloxy)benzoic acid (547 mg) in tetrahydrofuran (15 mL) stirred at room temp was added EDCI (767 mg) and HOBT (613 mg). The reaction mixture was stirred at room temperature for 2 h. Then ethyl 3-{7-[(Z)-(hydroxyamino)(imino)methyl]-1H-indol-3-yl}propanoate (D35) (551 mg) was added. The reaction mixture was stirred at 60° C. for 2 h, and then TBAF (2092 mg) was added. The reaction vessel was sealed and heated in Biotage Initiator using initial normal to 130° C. for 3 h. After cooling the reaction, the solvent was removed. Water (90 mL) and ethanol (30 mL) was added to the residue, a yellow solid was formed, filtered and dried in vacuo to gave the product ethyl 3-(7-{5-[3,4-bis(methyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-3-yl)propanoate (D67) (658 mg). δH (CDCl3, 400 MHz): 1.27 (3H, t), 2.76 (2H, t), 3.18 (2H, t), 4.01 (3H, s), 4.13 (3H, s), 4.16 (2H, q), 7.04 (1H, d), 7.20 (1H, d), 7.29 (1H, t), 7.74 (1H, d), 7.81 (1H, d), 7.90 (1H, dd), 8.14 (1H, dd), 9.63 (1H, s). MS (ES): C23H23N3O5 requires 421. found 422.2 (M+H+).

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