2-Amino-3-cyanopyridine-5-boronic Acid Pinacol Ester Chemical Properties

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

InChI

InChI=1S/C12H16BN3O2/c1-11(2)12(3,4)18-13(17-11)9-5-8(6-14)10(15)16-7-9/h5,7H,1-4H3,(H2,15,16)

InChIKey

KRNXYPYYVHFVQS-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(B2OC(C)(C)C(C)(C)O2)C=C1C#N

Safety Information

HS Code 

2933399990

2-Amino-3-cyanopyridine-5-boronic Acid Pinacol Ester Usage And Synthesis

Synthesis

2-amino-5-bromonicotinonitrile (50 g, 0.224 mol), bis (pinacolato) diboron (85.6 g, 0.337 mol), KOAc (44.1 g, 0.449 mol) and Pd (dppf) Cl2. CH2C12 (2.77 g, 3.4 mmol) was charged into a flask. Dioxane (400 mL) was added. The reaction mixture was stirred at 100 ℃ for 2 h under Ar. When LC-MS indicated that the reaction was completed, the mixture was cooled to room temperature. Subsequently, the mixture was filtered through diatomite, concentrated, diluted with a mixture of ethyl acetate and hexane (3:1, 1000 mL), filtered through silica gel (300-400 mesh), concentrated, crystallized and dried to give 2-Amino-3-cyanopyridine-5-boronic Acid Pinacol Ester (32 g, 66%) as a white solid.