Acetic Acid → furo(3,4-b)pyridin-5(7H)-one

Temperature

15 °C

A solution of furo[3,4-b]pyridine-5,7-dione (3.0 g, 20 mmol) in THF (20 mL) is treated with sodium borohydride (0.75 g, 20 mmol). The reaction mixture is placed under an argon atmosphere and the temperature is maintained at 15° C. with a water bath. Acetic acid (2.4 g, 39 mmol) is added dropwise at 15° C. The reaction mixture is stirred for 4 h and is then concentrated on a rotary evaporator. The crude residue is then treated with acetic acid (8 mL) and acetic anhydride (8.0 mL) and heated at 100° C. overnight. The reaction mixture is cooled and concentrated. The residue is purified by chromatography (silica gel, gradient elution 30% EtOAc/hexane to 50% EtOAc/hexane). The product containing fractions are concentrated to give the title compound as a white solid (360 mg, 27%).

1. concentrationis then concentrated on a rotary evaporator
2. additionThe crude residue is then treated with acetic acid (8 mL) and acetic anhydride (8.0 mL)
3. temperatureheated at 100° C. overnight
4. temperatureThe reaction mixture is cooled
5. concentrationconcentrated
6. customThe residue is purified by chromatography (silica gel, gradient elution 30% EtOAc/hexane to 50% EtOAc/hexane)
7. additionThe product containing fractions
8. concentrationare concentrated

ORD record

ord-4fe4798ab2db4e84b2ee0a68aeb0913f

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455535B2