Methanol → HCID 59146073, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoate (provided by WuxiPharma, China and made in a similar manner to D7) (4.0 g) in DCM (50 mL) at −78° C. under N2 atmosphere was added DIBAL-H (14 ml) dropwise. The reaction was stirred at −78° C. for 6 h. Then MeOH was added at −78° C. to quench the reaction. The resulting solution was concentrated. And the residue was purified by column chromatography on silical gel (15% EtOAc in hexane) to afford 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanal (D92) (1.3 g). δH (CDCl3, 400 MHz): 1.45 (6H, d), 2.90 (2H, t), 3.17 (2H, t), 4.72 (1H, m), 7.07 (1H, d), 7.16 (1H, d), 7.30 (1H, d), 7.78 (1H, d), 8.12 (2H, m), 8.29 (1H, s), 9.63 (1H, br s), 9.89 (1H, s). MS (ES): C22H20ClN3O3 requires 409; found 410 (M+H+).

Provenance & Evidence