2-(2-Methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical Properties

Boiling point:

450.6±55.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

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

pka

1.13±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C13H18BN5O2/c1-12(2)13(3,4)21-14(20-12)9-6-7-10(15-8-9)11-16-18-19(5)17-11/h6-8H,1-5H3

InChIKey

VOEFRGFXMMXFGK-UHFFFAOYSA-N

SMILES

C1(C2=NN(C)N=N2)=NC=C(B2OC(C)(C)C(C)(C)O2)C=C1

Safety Information

HS Code 

2931900090

2-(2-Methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridine Usage And Synthesis

Uses

2-(2-Methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine has been used to investigate torezolid -based antibacterial agent.

Synthesis

To a solution of 2-(2-methyl-tetrazolyl)-5-bromopyridine (1.00 g, 4.17 mmol) in dry degassed 1,4-dioxane (15 mL) was added bis(pinacolato)diboron (1.27 g, 5.00 mmol), potassium acetate (1.35 g, 13.75 mmol), and Pd(dppf)Cl2 (0.26 g, 0.35 mmol). The reaction mixture was placed in a sealed tube under argon protection and heated and stirred at 80°C for 3 hours. Upon completion of the reaction, the mixture was rapidly filtered through a silica gel column and dichloromethane was used as eluent. The organic layer was collected, concentrated under reduced pressure and the residue was washed with hexane to afford the white solid product 2-(2-methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1.03 g, 86.3% yield). The product was characterized by 1H-NMR (400 MHz, CDCl3): δ 9.14 (s, 1H), 8.30 (m, 2H), 4.48 (s, 3H), 1.38 (s, 12H).

References

[1] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 2, p. 143 - 146
[2] Patent: WO2008/108988, 2008, A1. Location in patent: Page/Page column 53
[3] European Journal of Organic Chemistry, 2016, vol. 2016, # 7, p. 1305 - 1313
[4] Patent: WO2009/74812, 2009, A1. Location in patent: Page/Page column 41
[5] Patent: US2010/69441, 2010, A1. Location in patent: Page/Page column 21-22

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