Hydrochloric Acid → 1H-Pyrrolo[2,3-c]pyridine, 4-broMo-5-Methoxy-

Temperature

90 °C

In A suspension of Iron powder (1.62 g, 28.9 mmol, 5.5 eq), [(E)-2-(3-Bromo-2-methoxy-5-nitro-pyridin-4-yl)-vinyl]-dimethyl-amine (1.59 g, 5.27 mmol), and EtOH (0.05M) were stirred while heating to 90° C. To the suspension was added dropwise concentrated HCl (1.6 mL) and the suspension refluxed (100° C.) for 2 hr. The reaction was cooled and neutralized by pouring reaction mixture into 200 mL of 1N NaOH and stirring. The resulting mixture was extracted with EtOAc (3×100 mL), the combined organics washed with brine and concentrated to a beige powder. The crude solid was further purified using chromatography eluting with EtOAc/Heptane giving 4-Bromo-5-methoxy-1H-pyrrolo[2,3-c]pyridine as a beige solid (0.980 g, 4.10 mmol, 78%). MS ESI m/z 229.2 (M+2H)+. 1NMR (400 MHz, CDCl3) δ 8.55 (br s, 1H), 8.36 (s, 1H), 7.47 (m, 1H), 6.60 (m, 1H), 4.12 (s, 3H).

1. temperaturethe suspension refluxed (100° C.) for 2 hr
2. temperatureThe reaction was cooled
3. additionby pouring
4. stirringstirring
5. extractionThe resulting mixture was extracted with EtOAc (3×100 mL)
6. washthe combined organics washed with brine
7. concentrationconcentrated to a beige powder
8. customThe crude solid was further purified
9. washeluting with EtOAc/Heptane

ORD record

ord-f3330a4ccf7444f8a2383e0176772ab7

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598217B2