Ethyl Acetate → 2-Methyl-1H-pyrrolo(2,3-c)pyridine

To a stirred solution of 3-Amino-4-picoline (7 g, 64.8 mmol) in anhydrous THF (200 mL), sec-BuLi (150 mL, 1.3M in cyclohexane, 194 mmol) was added dropwise over 20 minutes at −78° C. The solution was warmed to room temperature and stirred at 3 hours. Ethyl acetate (2.3 g, 25.9 mmol) was added dropwise into the reaction at −78° C. and the mixture was stirred at the same temperature for 2 hours. Methanol (50 mL) was added dropwise into the reaction over 10 minutes. The mixture was warmed to room temperature and stirred for 1 hour. A half-saturated NH4Cl (250 mL) was added. The mixture was extracted with EA. The combined organic layers were washed with brine, dried and concentrated to afford the crude product. The crude product was purified by silica gel chromatography (petroleum ether/ethyl acetate=10:1) to afford 2-methyl-1H-pyrrolo[2,3-c]pyridine (2.5 g, 73.5%).

1. stirringthe mixture was stirred at the same temperature for 2 hours
2. temperatureThe mixture was warmed to room temperature
3. stirringstirred for 1 hour
4. extractionThe mixture was extracted with EA
5. washThe combined organic layers were washed with brine
6. customdried
7. concentrationconcentrated
8. customto afford the crude product
9. customThe crude product was purified by silica gel chromatography (petroleum ether/ethyl acetate=10:1)

ORD record

ord-cebd969cfea04b20a42e5a54066b1371

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085583B2