6-bromoisoquinolin-3-amine Chemical Properties

Boiling point:

387.6±22.0 °C(Predicted)

Density 

1.649±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

4.49±0.38(Predicted)

form 

solid

color 

Light yellow

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933499090

6-bromoisoquinolin-3-amine Usage And Synthesis

Uses

6-Bromoisoquinolin-3-amine is employed in the comprehensive structure-activity relationship studies to identify the allosteric inhibitors that exhibit selective recognition of protein arginine methyltransferase PRMT3 in human cells.

Synthesis

General procedure for the synthesis of 6-bromoisoquinolin-3-amine from 1,6-dibromoisoquinolin-3-amine: 1,6-dibromoisoquinolin-3-amine (13.5 g, 45 mmol), ammonium formate (10.8 g, 172 mmol), and tetrakis(triphenylphosphine)palladium(0) (3.45 g, 3.0 mmol) were dissolved in 50 mL of DMF and the mixture was transferred to a 350 mL screw cap flask, sealed and heated at 50 °C for 48 hours. Subsequently, tetrakis(triphenylphosphine)palladium(0) (950 mg) and ammonium formate (3.0 g) were added supplementally to the reaction mixture and heating was continued at 50 °C for 48 hours. After completion of the reaction, the mixture was cooled to room temperature, the solid was collected by filtration, washed with a small amount of DMF and then with ether, and finally dried under vacuum at 50 °C to give the yellow amorphous solid product 6-bromoisoquinolin-3-amine (10.4 g, 90% yield). The product was detected by LCMS (API-ES), m/z: 222.9, 224.9 [M + 1]. 1H NMR (300MHz, DMSO-d6) δppm 8.81 (s, 1H), 7.80 (d, J = 1.6Hz, 1H), 7.73 (d, J = 8.8Hz, 1H), 7.22 (dd, J = 8.6, 1.9 Hz, 1H), 6.55 (s, 1H), 6.12 (s, 2H).

References

[1] Patent: WO2009/11871, 2009, A2. Location in patent: Page/Page column 188; 189
[2] Patent: WO2009/11880, 2009, A2. Location in patent: Page/Page column 159-160

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