7-BROMO-1H-PYRROLO[2,3-C]PYRIDINE Chemical Properties

Melting point:

174-178°C

Boiling point:

362.0±22.0 °C(Predicted)

Density 

1.770±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

solid

pka

12.99±0.40(Predicted)

Appearance

Yellow to brown Solid

Safety Information

Hazard Codes 

T

Risk Statements 

25-37/38-41

Safety Statements 

26-36/37/39-45

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

HS Code 

2933399990

7-BROMO-1H-PYRROLO[2,3-C]PYRIDINE Usage And Synthesis

Synthesis

Example 1: Synthesis of [1-(4-methoxy-benzenesulfonyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]-phenyl-amine (Compound 1); 7-bromo-6-azaindole (2 in Scheme 1): 2-bromo-3-nitropyridine (1 in Schemes 1,2, 2.0 g, 98%, 9.7 mmol) was dissolved in anhydrous THF (80 mL) and cooled the solution to -78 °C. An excess of vinyl magnesium bromide (1.0 M solution of THF, 40 mL, 40 mmol) was slowly added under nitrogen protection. The reaction mixture was stirred at -40 to -50 °C for 1 h. The reaction was subsequently quenched with saturated NaHCO3 solution. The organic and aqueous layers were separated and the aqueous layer was extracted with EtOAc (3 times). The organic layers were combined, dried with anhydrous MgSO4, filtered and the filtrate concentrated. The residue was purified by fast chromatography (eluent: EtOAc/hexane=1:2) to afford the target product 2 (1.1 g, 60%).1H NMR (500 MHz, CDCl3): δ 6.66 (dd, 1H, J=2.9,2.1Hz), 7.43 (dd, 1H, J=2.9,2.1Hz), 7.51 (d, 1H, J =5.2Hz), 8.03 (d, 1H, J=5.3Hz), 8.79 (br, 1H).

References

[1] Patent: WO2011/19634, 2011, A2. Location in patent: Page/Page column 13

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