Hydrochloric Acid → HCID 178428619, compound

Participants

Reaction Conditions

Reaction Steps

N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-(2-oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-benzamide (as prepared above in Step 4; 0.300 g, 0.793 mmol) was dissolved in anhydrous ethanol (8 mL) and the resulting solution was treated with ethyl formate (0.058 mL, 0.717 mmol) The resulting solution was treated in dropwise fashion with a 21 wt % solution of sodium ethoxide in ethanol (1.48 mL, 3.97 mmol). This reaction mixture was heated at 78° C. for 0.5 h, which caused the reaction mixture to turn black in color. Subsequently, the reaction mixture was cooled to room temperature, and then the reaction pH was adjusted to pH=1 with dropwise addition of 1M HCl(aq). The reaction mixture was diluted with EtOAc (25 mL) and extracted with brine (2×25 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified via flash silica gel chromatography (5% MeOH in CHCl3) affording the title compound in 19% yield (0.061 g, 0.150 mmol).

Provenance & Evidence