Water → 7-chloro-1-methyl-1H-pyrrolo[2,3-c]pyridine

Temperature

0 °C

To a solution of 7-chloro-1H-pyrrolo[2,3-c]pyridine (3.00 g, 19.7 mmol) in THF (30 mL) cooled to 0° C. was added 60% NaH in mineral oil (0.940 g, 23.6 mmol NaH). The reaction mixture was stirred at 0° C. for 20 minutes. Iodomethane (6.20 g, 43.7 mmol) was added and the reaction mixture was stirred at 0° C. for 1 h and at 20° C. for 2 h. The mixture was poured into water (20 mL) and extracted with EtOAc (3×20 mL). The organic layers were dried over Na2SO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography, eluting with a gradient of 17-33% EtOAc/petroleum ether to give the title compound as a yellow solid (2.8 g, 85%).

1. stirringthe reaction mixture was stirred at 0° C. for 1 h and at 20° C. for 2 h
2. extractionextracted with EtOAc (3×20 mL)
3. dry with materialThe organic layers were dried over Na2SO4
4. filtrationfiltered
5. concentrationthe filtrate was concentrated in vacuo
6. customThe residue was purified by silica gel column chromatography
7. washeluting with a gradient of 17-33% EtOAc/petroleum ether

ORD record

ord-08b673aa83ec42d3a2c60451fce16911

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227956B2