1H-pyrrolo[2,3-c]pyridine-4-carbonitrile

Synthesis

Step 1: In a dry reaction flask, 4-bromo-1H-pyrrolo[2,3-c]pyridine (320 mg, 1.62 mmol), Pd(dppf)Cl2 (131 mg, 0.179 mmol), zinc cyanide (190 mg, 1.62 mmol) and zinc powder (21 mg, 0.324 mmol) were dissolved in DMF (20 mL). The reaction mixture was stirred at 120 °C for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and quenched by adding water (100 mL). The reaction mixture was extracted with ethyl acetate (3 x 50 mL) and the organic layers were combined. The organic layer was concentrated under reduced pressure and the crude product obtained was purified by silica gel column chromatography with the eluent of petroleum ether/ethyl acetate (1:1, v/v) to give 232 mg (99.8% yield) of 1H-pyrrolo[2,3-c]pyridine-4-carbonitrile as a yellow solid. Mass spectrum (ESI) m/z: 144.2 [M + 1]+.

References

[1] Patent: WO2013/92940, 2013, A1. Location in patent: Page/Page column 38
[2] Patent: WO2018/11628, 2018, A1. Location in patent: Paragraph 00639
[3] Patent: WO2010/145201, 2010, A1. Location in patent: Page/Page column 25-26