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

Melting point:

234-239 °C

Boiling point:

324℃

Density 

2.52

Flash point:

150℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

11.42±0.40(Predicted)

color 

Off-white to light yellow

Sensitive 

Light Sensitive

InChI

InChI=1S/C7H4BrIN2/c8-4-1-5-6(9)3-11-7(5)10-2-4/h1-3H,(H,10,11)

InChIKey

GIPGJYARDOQGDJ-UHFFFAOYSA-N

SMILES

C12NC=C(I)C1=CC(Br)=CN=2

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:ALFA

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

Uses

5-Bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine is a useful intermediate for organic synthesis.

Synthesis

General procedure for the synthesis of 5-bromo-3-iodo-7-azaindole from 5-bromo-7-azaindole: Preparation of 5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (Intermediate A) [0442]. 5-Bromo-1H-pyrrolo[2,3-b]pyridine (10 g, 50.76 mmol) was dissolved in 500 mL of acetone with stirring, followed by the addition of N-iodosuccinimide. The reaction mixture was stirred at room temperature for 20 min. Upon completion of the reaction, the product was pulverized, the white solid was collected by filtration and washed with 100 mL of acetone. The resulting solid was dried under vacuum to afford 5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (16.34 g, 100% yield) as a light yellow powder.1H NMR (DMSO-d6, 300 MHz) δ 8.51 (d, J = 2.1 Hz, 1H), 8.22 (s, 1H), 8.02 (d, J = 1.2 Hz, 1H), 8.00 (d, J = 5.1 Hz, 2H), 7.44 (dd, J = 8.7 Hz, 0.6 Hz, 2H), 2.35 (s, 3H); MS ESI (m/z): 322/324 [M + H]+, calculated value 322.

References

[1] Patent: WO2011/149950, 2011, A2. Location in patent: Page/Page column 162
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9569 - 9585
[3] Patent: WO2014/85795, 2014, A1. Location in patent: Paragraph 0400
[4] Patent: US2015/307492, 2015, A1. Location in patent: Paragraph 0120-0125
[5] Patent: WO2016/26078, 2016, A1. Location in patent: Paragraph 076

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