6-Chloro-5-azaindole

Uses

6-Chloro-5-azaindole is used in preparation of oxodiphenyldihydropyrazolecarboxamide derivatives and analogs for use as ACSS2 inhibitors.

Synthesis

2-Chloro-5-[(E)-2-ethoxyvinyl]pyridin-4-amine (CAS:1190862-36-2, 1.00 g, 5.30 mmol) was used as a raw material, which was dissolved in methanol (20 mL), followed by the addition of concentrated hydrochloric acid (1.00 mL, 32.64 mmol). The reaction mixture was stirred at 75°C for 21 hours. Upon completion of the reaction, the mixture was concentrated under reduced pressure, neutralized with saturated aqueous potassium carbonate solution and then extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give 6-chloro-5-azaindole (0.76 g, 99% yield) as a beige solid. The product was detected by mass spectrometry (LRMS), m/z: 153 (M + 1)+; 1H-NMR (CDCl3) δ: 6.65 (m, 1H), 7.20 (s, 2H), 8.60 (m, 2H).

References

[1] Patent: EP2108641, 2009, A1. Location in patent: Page/Page column 49-50