5-Methyl-1H-pyrrolo[2,3-b]pyridine

Chemical Properties

5-METHYL-1H-PYRROLO[2,3-B]PYRIDINE is Light yellow solid

Uses

5-METHYL-1H-PYRROLO[2,3-B]PYRIDINE is an intermediate for preparation of pyrrolopyridine compounds as protein kinase modulators useful in treatment of diseases associated with aberrant activity of protein kinases.

Synthesis

The general procedure for the synthesis of 5-methyl-7-azaindole from 5-methyl-3-((trimethylmethylsilyl)alkynyl)pyridin-2-amine was as follows: 5-methyl-3-((trimethylsilyl)alkynyl)pyridin-2-amine (9.8 g, 48.0 mmol) and N-methylpyrrolidinone (50 mL) were added to a dry three-necked flask. Under ice bath conditions, sodium hydride (60% dispersed in mineral oil, 2.8 g, 59 mmol) was slowly added, followed by heating the reaction mixture to 100 degrees Celsius and holding for 10 minutes. Upon completion of the reaction, the mixture was cooled to room temperature and saturated ammonium chloride solution (50 mL) was slowly added to quench the reaction. Extraction was performed with ethyl acetate (50 mL x 3) and the organic phases were combined. The organic phase was washed sequentially with water (100 mL) and saturated brine (100 mL) and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to dryness in a rotary evaporator to obtain the crude product. The crude product was recrystallized with ethyl acetate (10 mL) to give 5-methyl-7-azaindole (5.1 g, 38.6 mmol, 80% yield) as a white solid.

References

[1] Patent: CN107056781, 2017, A. Location in patent: Paragraph 0008
[2] Patent: WO2017/133667, 2017, A1. Location in patent: Page/Page column 120
[3] Patent: US2009/253679, 2009, A1. Location in patent: Page/Page column 41
[4] Patent: WO2008/4117, 2008, A1