3-Amino-4-fluorophenylboronic acid, pinacol ester Chemical Properties

Melting point:

54.0-55.1 °C

Boiling point:

336.8±32.0 °C(Predicted)

Density 

1.11±0.1 g/cm3(Predicted)

storage temp. 

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

form 

Solid

pka

3.19±0.10(Predicted)

Appearance

White to off-white Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HS Code 

2931900090

3-Amino-4-fluorophenylboronic acid, pinacol ester Usage And Synthesis

Uses

3-Amino-4-fluorophenylboronic Acid Pinacol Ester is used as a reactant in preparation of LY3009120 as pan-RAF inhibitor with activity against BRAF or RAS mutant tumor cells.

Synthesis

General procedure for the synthesis of 3-amino-4-fluorophenylboronic acid pinacol ester from 2-(4-fluoro-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl: First, a 500-mL Parr reactor flask was purged with nitrogen and 2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- based) aniline (13) (6.92 g, 25.9 mmol), ethyl acetate (150 mL) and 10% palladium carbon (50% wet, 150 mg dry wt.). Subsequently, the reaction flask was connected to a Parr hydrogenation unit, evacuated and filled with hydrogen to a pressure of 50 psi and reacted under shaking conditions for 2 hours. Upon completion of the reaction, the hydrogen was evacuated and filled with nitrogen. The catalyst was removed by filtration through a diatomaceous earth pad (521) and the filter cake was washed with dichloromethane (400 mL). The resulting filtrate was concentrated under reduced pressure to afford the target product 3-amino-4-fluorophenylboronic acid pinacol ester (14) in 100% yield (6.34 g) as a yellow oil. The product was characterized by 1H NMR (500 MHz, CDCl3): δ 7.22 (dd, 1H, J = 8.5,1.0 Hz), 7.16 (m, 1H), 6.97 (dd, 1H, J = 11.5,8.0 Hz), 3.68 (br s, 2H), 1.33 (m, 12H); MS (ESI+) m/z 238.2 (M + H).

References

[1] Patent: WO2010/56875, 2010, A1. Location in patent: Page/Page column 205

3-Amino-4-fluorophenylboronic acid, pinacol ester(1003575-43-6)Related Product Information

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