Furo[3,4-b]pyridin-5(7H)-one

Furo[3,4-b]pyridin-5(7H)-one Property

Melting point:

142-144 °C

Boiling point:

330.9±37.0 °C(Predicted)

Density 

1.360±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

1.81±0.20(Predicted)

Appearance

White to off-white Solid

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.

Furo[3,4-b]pyridin-5(7H)-one Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of furan[3,4-B]pyridin-5(7H)-one from 2,3-pyridinedicarboxylic anhydride: NaBH4 (1.14 g, 33.5 mmol) was slowly added to a solution of tetrahydrofuran (THF, 35 mL) of 2,3-pyridinedicarboxylic anhydride (5.0 g, 33.5 mmol) under argon gas protection and the temperature of the reaction was kept at 15 °C. Subsequently, acetic acid (4 g, 67 mmol) was added dropwise and the reaction mixture was stirred continuously at 15 °C for 4 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in a mixture of acetic acid (13.5 mL) and acetic anhydride (13.5 mL) and stirred at 100 °C for 3 hours. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in a mixed solution of water (35 mL) and sodium chloride (6.7 g). The aqueous phase was extracted with chloroform (3 x 40 mL) and the organic layers were combined and concentrated. Finally, recrystallization by isopropanol (z'-PrOH) afforded the target compound furan[3,4-B]pyridin-5(7H)-one (2.5 g, 55% yield) as a light yellow solid with a melting point of 123-125°C. The product was detected by IR (KBr), showing characteristic absorption peaks located at 1778, 1567, 1423, 1355, 1000, 743 cm^-1 ; 1H NMR (300 MHz, CDCl3) spectrum showed δ 8.87 (dd, J = 1.5, 4.9 Hz, 1H), 8.22 (dd, J = 1.5, 7.7 Hz, 1H), and 7.50 (dd, J = 5.0, 7.8 Hz, 1H), 5.33 (s, 2H); ESIMS analysis showed m/z 136 (MH+, relative intensity 100).

References

[1] Journal of Medicinal Chemistry, 2009, vol. 52, # 6, p. 1778 - 1782
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 8, p. 3840 - 3853
[3] Patent: WO2017/160898, 2017, A1. Location in patent: Paragraph 00104; 00120
[4] Synthesis, 1997, # 1, p. 113 - 116
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 3012 - 3015