1-BOC-5-chloroindole-3-boronic acid, pinacol ester

1-BOC-5-chloroindole-3-boronic acid, pinacol ester Property

Boiling point:

479.5±48.0 °C(Predicted)

Density 

1.16±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

Appearance

White to off-white Solid

Safety

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1-BOC-5-chloroindole-3-boronic acid, pinacol ester Chemical Properties,Usage,Production

Synthesis

GENERAL STEPS: Pd(dppf)Cl2 (29 mg, 0.04 mmol, 3 mol%) and tert-butyl 5-chloro-3-iodo-1H-indole-1-carboxylate (500 mg, 1.32 mmol) were added to a dry screw-capped reaction flask equipped with a septum under argon protection. Subsequently, anhydrous toluene (6.5 mL) was added and the mixture was degassed with argon for 5 minutes. Under argon atmosphere, dry triethylamine (0.7 mL) and 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.3 mL, 2 mmol) were added sequentially. The reaction mixture was placed in an oil bath preheated to 80 °C and stirred for 3 h. The reaction progress was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the residue was purified by fast column chromatography (eluent: hexane/ethyl acetate = 10/1) to afford the target product 1-Boc-5-chloroindole-3-boronic acid pinacol ester (418 mg, 84% yield). The product characterization data were consistent with those reported in the literature.1H NMR (500 MHz, CDCl3) δ 8.08 (d, J=8.8 Hz, 1H), 8.00 (s, 1H), 7.95 (d, J=2.1 Hz, 1H), 7.26 (dd, J=8.8,2.1 Hz, 1H), 1.65 (s, 9H), 1.38 (s, 12H).

References

[1] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 5, p. 1622 - 1629
[2] European Journal of Organic Chemistry, 2011, # 24, p. 4532 - 4535
[3] European Journal of Organic Chemistry, 2013, # 21, p. 4564 - 4569