2-(Pinacolateboryl)indole Chemical Properties

Melting point:

84-85 °C

Boiling point:

396 °C

Density 

1.11

Flash point:

193 °C

storage temp. 

Inert atmosphere,2-8°C

pka

16.76±0.30(Predicted)

form 

solid

Appearance

White to off-white Solid

Safety Information

WGK Germany 

3

HS Code 

2933998090

2-(Pinacolateboryl)indole Usage And Synthesis

Synthesis

General procedure for the synthesis of indole-2-boronic acid pinacol ester from indole and bis-boronic acid pinacol ester: Dimethyl(1,5-cyclooctadiene)iridium(I) (64 mg, 0.096 mmol) and 4,4'-di-tert-butyl-2,2'-bipyridine (52 mg, 0.19 mmol) were added to a dry, round-bottomed flask under argon gas protection. The flask was evacuated and backfilled three times with argon. Indole (1.50 g, 12.8 mmol) and bis(pinacolato)diboron (1.62 g, 6.40 mmol) were then added and the flask was again purged with argon. Anhydrous hexane (38.5 mL) was injected and the reaction mixture was stirred for 8 hours at room temperature in an argon atmosphere. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent: 0-10% ethyl acetate/hexane) to afford indole-2-boronic acid pinacol ester (2.66 g, 85% yield). The product was characterized by 1H NMR (300 MHz, d6-DMSO): δ 11.27 (s, 1H), 7.55 (d, J = 7.9 Hz, 1H), 7.38 (dd, J = 8.2, 0.8 Hz, 1H), 7.15-7.06 (m, 1H), 7.00-6.92 (m, 1H), 6.90-6.87 (m, 1H) , 1.32 (s, 12H).

References

[1] Journal of the American Chemical Society, 2015, vol. 137, # 7, p. 2665 - 2673
[2] Patent: WO2014/22744, 2014, A1. Location in patent: Paragraph 0117
[3] Journal of the American Chemical Society, 2014, vol. 136, # 18, p. 6566 - 6569
[4] Dalton Transactions, 2015, vol. 44, # 29, p. 13007 - 13016
[5] Organic Letters, 2012, vol. 14, # 16, p. 4266 - 4269

2-(Pinacolateboryl)indole(476004-81-6)Related Product Information

• Indole
• Indole-3-butyric acid
• Indometacin
• Indole-3-acetic acid
• Bis(pinacolato)diboron
• Indole-6-boronic acid pinacol ester
• ISOINDOLIN-5-OL HCL
• Methyl indole-2-carboxylate
• INDOLE-2,5-DICARBOXYLIC ACID 2-ETHYL ESTER 5-METHYL ESTER
• DIMETHYL INDOLE-2,3-DICARBOXYLATE
• IMIDAZO[1,2-A]PYRAZINE
• (1H-INDOL-3-YL)METHANAMINE
• INDOLE-3-PROPIONAMIDE
• INDOLE-5-METHANOL
• Indole-4-boronic acid
• PINACOL ESTER INDOLE-5-BORONIC ACID
• 1H-INDOL-3-YLBORONIC ACID
• 6-HYDROXYMETHYLINDOLE