Methanol → Methyl 2-(5-bromopyridin-3-yl)acetate

Temperature

0 °C

To a suspension of 2-(5-bromopyridin-3-yl)acetic acid (5 g, 23.14 mmol) in MeOH (100 mL) was added thionyl chloride (1.858 mL, 25.5 mmol) at 0° C., and the mixture was stirred at 0° C. for 2 h. The mixture was concentrated in vacuo, re-dissolved in DCM (100 mL) and MeOH (10 mL), and saturated NaHCO3 in water (5 mL) was added, followed with NaHCO3 (10 g). To the mixture was added silica gel (10 g) and the mixture was concentrated. The residue was purified by silica chromatography eluting with 0-50% EtOAc-heptane to give methyl 2-(5-bromopyridin-3-yl)acetate. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.64 (s, 3H), 3.80 (s, 2H), 8.01 (dd, J=2.0 Hz, 1H), 8.48 (d, J=1.8 Hz, 1H), 8.61 (d, J=2.3 Hz, 1H).

1. concentrationThe mixture was concentrated in vacuo
2. dissolutionre-dissolved in DCM (100 mL)
3. additionMeOH (10 mL), and saturated NaHCO3 in water (5 mL) was added
4. additionTo the mixture was added silica gel (10 g)
5. concentrationthe mixture was concentrated
6. customThe residue was purified by silica chromatography
7. washeluting with 0-50% EtOAc-heptane

ORD record

ord-f5461e55865d4fb4a6e353b83020582c

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08519142B2