Potassium Carbonate → 4-bromo-1-(2-hydroxyethyl)pyridin-2(1H)-one

Temperature

80 °C

To a solution of 4-bromopyridin-2(1H)-one (174 mg, 1.00 mmol) in THF (3.5 mL) was added K2CO3 (1.38 g, 10.0 mmol) and 2-iodoethanol (156 μL, 2.00 mmol). The reaction was stirred at 80° C. for 2 days before being cooled to room temperature and filtered. The filtrate was concentrated and purified by column chromatography (0-10% MeOH—CH2Cl2) to yield 4-bromo-1-(2-hydroxyethyl)pyridin-2(1H)-one as a pale yellow solid (30 mg, 7%). ESI-MS m/z calc. 217.0. found 218.3 (M+1)+. Retention time 0.33 minutes. 1H NMR (400 MHz, DMSO-d6) δ 7.57 (d, J=7.2 Hz, 1H), 6.70 (d, J=2.2 Hz, 1H), 6.44 (dd, J=2.2, 7.2 Hz, 1H), 4.89 (t, J=5.4 Hz, 1H), 3.91 (t, J=5.4 Hz, 2H), 3.59 (q, J=5.4 Hz, 2H).

1. temperaturebefore being cooled to room temperature
2. filtrationfiltered
3. concentrationThe filtrate was concentrated
4. custompurified by column chromatography (0-10% MeOH—CH2Cl2)

ORD record

ord-35ef8e46d9514ff6ba086e7a576277ca

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969386B2