2-HYDROXY-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE Chemical Properties

Melting point:

197-198

Density 

1.10±0.1 g/cm3(Predicted)

storage temp. 

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

pka

11.98±0.10(Predicted)

form 

solid

color 

White

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-38-36

Safety Statements 

26-36/37/39

WGK Germany 

2

HS Code 

2933399990

2-HYDROXY-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE Usage And Synthesis

Uses

6-Hydroxypyridine-3-boronic acid pinacol ester can be used as a reactant:

• In the synthesis of novel glutamate transporter EAAT2 activators.
• To prepare crizotinib derivatives as SHIP2 inhibitors.

Uses

2-HYDROXY-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE is used in the preparation of modified C3 Betulinic acid (B330250) derivatives as HIV maturation inhibitors.

Synthesis

Using 2-hydroxy-5-bromopyridine (SM1, 0.1 g, 0.57 mmol) and pinacol ester of bisboronic acid (SM2, 0.88 g, 3.45 mmol) as raw materials, under argon protection, SM1, SM2, tricyclohexylphosphine (0.032 g, 0.114 mmol), Pd2(dba)3 (0.052 g, 0.057 mmol) and KOAc (0.17 g, 1.71 mmol) were dissolved in dioxane (10 mL). The reaction mixture was transferred to a sealed tube and the reaction was stirred at 110 °C overnight. The progress of the reaction was monitored by LC-MS and after confirming complete consumption of the feedstock, the solvent was removed under reduced pressure. The residue was diluted with brine and extracted with EtOAc. The organic phases were combined, dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (eluent: 50% EA/PE) to afford the target compound 2-hydroxypyridine-5-boronic acid pinacol ester (Compound 3, 0.08 g, 64%) as a black liquid.

References

[1] Patent: WO2016/44770, 2016, A1. Location in patent: Page/Page column 644

2-HYDROXY-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE(1054483-78-1)Related Product Information

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