5-BROMO-1-TRIISOPROPYLSILANYL-1H-PYRROLO[2,3-B]PYRIDINE Chemical Properties

Boiling point:

333.7±35.0 °C(Predicted)

Density 

1.19±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

form 

solid

pka

2.87±0.30(Predicted)

Appearance

off-white solid

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2933998090

5-BROMO-1-TRIISOPROPYLSILANYL-1H-PYRROLO[2,3-B]PYRIDINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 1-triisopropylsilyl-5-bromo-7-azaindole from triisopropylchlorosilane: Sodium hydride (0.63 g, 25.15 mmol) was added batchwise to a stirred solution of tetrahydrofuran (THF, 50 mL) of 5-bromo-7-azaindole (3.3 g, 16.75 mmol) at room temperature with continuous stirring for 15 min. Subsequently, triisopropylchlorosilane (5.3 mL, 25.15 mmol) was added and the reaction mixture was heated to 80 °C and maintained for 3 hours. After completion of the reaction, the solvent was removed by evaporation and the residue was dissolved in water (50 mL). The aqueous layer was extracted with ethyl acetate (EtOAc, 3 x 50 mL) and the organic phase was dried with anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The crude product was purified by Biotage HPFC system (eluent: 10% ethyl acetate/hexane) to afford the target compound 5-bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine as a white solid (5.2 g, 88% yield). Mass spectrometry analysis showed the molecular ion peak m/z 355 (M + 1).

References

[1] Patent: WO2005/103050, 2005, A2. Location in patent: Page/Page column 180
[2] Patent: WO2006/128692, 2006, A2. Location in patent: Page/Page column 158
[3] Patent: US2007/49615, 2007, A1. Location in patent: Page/Page column 62-63
[4] Patent: US2007/49615, 2007, A1. Location in patent: Page/Page column 68

5-BROMO-1-TRIISOPROPYLSILANYL-1H-PYRROLO[2,3-B]PYRIDINE(858116-66-2)Related Product Information

• 5-bromo-1,2-dihydro-3H-Pyrazolo[3,4-b]pyridin-3-one
• Tiotropium bromide
• 5-BROMO-3-IODO-1-TRIISOPROPYLSILANYL-1H-PYRROLO[2,3-B]PYRIDINE
• 5-Bromo-7-azaindole
• 5-BROMO-1-TRIISOPROPYLSILANYL-1H-PYRROLO[2,3-B]PYRIDINE
• 1-(TRIISOPROPYLSILYL)PYRROLE