Methoxymethyl-triphenylphosphonium chloride → HCID 59146072, compound

Participants

Reaction Steps

To a solution of (methoxymethyl)triphenylphosphonium chloride (2.9 g) in dimethyl sulfoxide (20 mL) stirred under nitrogen at 20° C. was added a solution of NaHMDS (8.6 mL, 1.0 mol/L in THF) dropwise during 5 mins. The reaction mixture was stirred at this temperature for 20 mins. Then 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole-3-carbaldehyde (D87) (1.4 g) was added in one portion. The mixture was stirred at room temperature for 30 mins. The reaction mixture was quenched with water, partitioned between ether (100 mL) and water (50 mL). The organic phase was washed with water and brine, dried over sodium sulphate and evaporated to afford 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-3-[(E)-2-(methyloxy)ethenyl]-1H-indole (D87) as a brown oil (3.8 g), used directly in the next step. MS (ES): C23H22ClN3O3 requires 423; found 424.2 (M+H+).

Provenance & Evidence