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Beige powder

tert-Butyl 3-Formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate is a useful reagent in study of eletrophilic fragment-based design of reversible covalent kinase inhibitors.

To a round bottom flask was added 1H-pyrrolo[2,3-B]pyridine-3-carboxaldehyde (6.6 g, 45 mmol), di-tert-butyl dicarbonate (10.7 g, 50 mmol), 4-dimethylaminopyridine (55 mg, 0.45 mmol), and triethylamine (13 g, 130 mmol), followed by methylene chloride (50 mL). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the mixture was concentrated to dryness and purified by fast column chromatography to afford the target product 1-Boc-7-azaindole-3-carbaldehyde (9.8 g, 89% yield).

[1] Patent: WO2011/23081, 2011, A1. Location in patent: Page/Page column 55
[2] Patent: WO2017/37116, 2017, A1. Location in patent: Page/Page column 143
[3] Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1531 - 1536
[4] Patent: WO2011/20193, 2011, A1. Location in patent: Page/Page column 36
[5] Patent: WO2013/45516, 2013, A1. Location in patent: Page/Page column 129; 197