反应详情

温度

50 °C

Ethyl 3-(7-{5-[3,4-bis(ethyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-3-yl)propanoate (100 mg) (D66), DABCO (13 mg) and N,N-dimethylformamide (4 mL) was added to dimethyl carbonate (10 mL) successively. The reaction vessel was sealed and heated in Biotage Initiator using initial normal to 150° C. for 2 h. After cooling the reaction, the solvent was removed in vacuo. The residue was dissolved in tetrahydrofuran (5 mL) and methanol (5 mL), and then NaOH (27 mg) in water (5 mL) was added. The mixture was stir at 50° C. for 8 h. The organic solvent was evaporated off and the mixture was acidified with HCl (1 M) solution to pH around 1. Extracted with EtOAc (60 mL), the organic layer was separated and the organic solvent was evaporated off. The residue was purified by Mass Directed Auto Prep to afford 3-(7-{5-[3,4-bis(ethyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1-methyl-1H-indol-3-yl)propanoic acid (E42) (50 mg). δH (DMSO-d6, 400 MHz): 1.35-1.39 (6H, m), 2.61 (2H, t), 2.97 (2H, t), 3.63 (3H, s), 4.12-4.19 (4H, m), 7.15-7.22 (3H, m), 7.43 (1H, dd), 7.65 (1H, d), 7.78 (1H, dd), 7.79 (1H, dd), 12.06 (1H, br s). MS (ES): C24H25N3O5 requires 435; found 436.2 (M+H+).

1. customThe reaction vessel was sealed
2. temperatureheated in Biotage Initiator
3. customnormal to 150° C.
4. customfor 2 h
5. temperatureAfter cooling
6. customthe reaction
7. customthe solvent was removed in vacuo
8. dissolutionThe residue was dissolved in tetrahydrofuran (5 mL)
9. additionmethanol (5 mL), and then NaOH (27 mg) in water (5 mL) was added
10. customThe organic solvent was evaporated off
11. extractionExtracted with EtOAc (60 mL)
12. customthe organic layer was separated
13. customthe organic solvent was evaporated off
14. customThe residue was purified by Mass Directed Auto Prep