4-Fluoroindole

Chemical Properties

Beige low melting solid

Uses

Reactant for preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators 1 Reactant for preparation of antifungal agents 2 Reactant for preparation of Sodium-Dependent Glucose Co-transporter 2 (SGLT2) Inhibitors for the Management of Hyperglycemia in Diabetes 3 Reactant for preparation of Potent Selective Serotonin Reuptake Inhibitors 4 Reactant for preparation of Inhibitors of HIV-1 attachment 5 Reactant for preparation of monoamine reuptake inhibitors 6 Reactant for preparation of histone deacetylase (HDAC) inhibitors 7 Reactant for preparation of inhibitors of proliferation of human breast cancer cells.

Synthesis

A suspension was prepared from 1-[2-(2-fluoro-6-nitrophenyl)vinyl]pyrrolidine (6 g, 25.42 mmol) in methanol (50 mL). To this suspension, Raney nickel (500 mg) was added and the hydrogenation reaction was carried out at atmospheric pressure at ambient temperature for 20 hours. After completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad and the filtrate was collected. The filtrate was concentrated under vacuum to afford the target product 4-fluoro-1H-indole (2.05 g, 60% yield) as a brown liquid.

References

[1] Patent: WO2009/130481, 2009, A1. Location in patent: Page/Page column 149-150
[2] Patent: JP2016/204312, 2016, A. Location in patent: Paragraph 0026; 0071; 0076; 0079; 0085