Iodine → HCID 59146064, compound

Participants

Reaction Steps

To a suspension of NaBH4 (0.52 g) in THF (50 mL) was added a solution of 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]propanoic acid (E2) (1.5 g) in THF (20 mL) dropwise. The mixture was stirred for 15 mins and a solution of I2 (1.7 g) in THF (90 mL) was added dropwise. The reaction mixture was stirred at 20° C. for 20 h. The reaction mixture was quenched with water, the solvent was evaporated and the residue was partitioned between ethyl acetate (100 mL) and water (50 mL). The organic phase was washed with aqueous HCl (2 M), water and brine, dried over sodium sulphate and evaporated to give the crude product as yellow foam, which was purified by column chromatography (15% EtOAc in hexanes) to afford 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]-1-propanol (D128) (900 mg). δH (DMSO-d6, 400 MHz): 1.35 (6H, d), 1.80 (2H, m), 2.75 (2H, t), 3.48 (2H, t), 3.60 (3H, s), 4.47 (1H, t), 4.88 (1H, m), 7.16 (2H, m), 7.43 (2H, m), 7.77 (1H, d), 8.12 (1H, dd), 8.19 (1H, d). MS (ES): C23H24ClN3O3 requires 425; found 426.2 (M+H+).

Provenance & Evidence