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

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

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

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

Furo[3,4-b]pyridin-5(7H)-one(5657-51-2)Related Product Information

• Amiodarone
• Chromium picolinate
• Zinc pyrithione
• Furaltadone
• Sulfasalazine
• 2,3-Pyridinedicarboxylic anhydride
• spiro(9h-benzo(a)fluorene-9,2’(3’h)-furo(3,2-b)-pyridin)-11(1h)-one,2,3,3’a,4
• 7-[4-(Diethylamino)-2-ethoxyphenyl]-7-(2-methyl-1-octyl-1H-indol-3-yl)furo[3,4-b]pyridin-5(7H)-one
• Furo[2,3-c]pyridin-7(6H)-one, 2,3-dihydro- (9CI)
• Furo[3,2-b]pyridin-3(2H)-one,2-methyl-(9CI)
• Phthalide
• 7-[4-(Diethylamino)-2-methylphenyl]-7-(1-ethyl-2-methyl-1H-indol-3-yl)furo[3,4-b]pyridin-5(7H)-one
• Furo[3,2-c]pyridin-4(5H)-one,7-methyl-(9CI)
• FURO[2,3-C]PYRIDIN-3(2H)-ONE HYDROCHLORIDE
• FURO[3,4-C]PYRIDIN-3(1H)-ONE
• 7-[4-(diethylamino)-2-ethoxyphenyl]-7-(1-ethyl-2-methyl-1H-indol-3-yl)furo[3,4-b]pyridin-5(7H)-one
• 5-[4-(diethylamino)-2-ethoxyphenyl]-5-(1-ethyl-2-methyl-1H-indol-3-yl)furo[3,4-b]pyridin-7(5H)-one
• Furo[2,3-c]pyridin-3(2H)-one (9CI)