1-(tert-Butoxycarbonyl)-3-formyl-7-azaindole, 3-Formyl-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester Chemical Properties

Melting point:

124-129 °C

Boiling point:

389.6±45.0 °C(Predicted)

Density 

1.20±0.1 g/cm3(Predicted)

storage temp. 

2-8°C, stored under nitrogen

pka

1.35±0.30(Predicted)

form 

powder

Appearance

White to off-white Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-43

Safety Statements 

36/37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

1-(tert-Butoxycarbonyl)-3-formyl-7-azaindole, 3-Formyl-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester Usage And Synthesis

Chemical Properties

Beige powder

Uses

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.

Synthesis

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).

References

[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

1-(tert-Butoxycarbonyl)-3-formyl-7-azaindole, 3-Formyl-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester(144657-66-9)Related Product Information

• 7-Azaindole
• 1-Boc-7-azaindole
• 7-AZAINDOLE-3-CARBOXALDEHYDE