Methyl iodide → 4,6-Dichloro-1-methyl-1H-pyrrolo[3,2-c]pyridine

Temperature

0 °C

A solution of 4,6-dichloro-1H-pyrrolo[3,2-c]pyridine (270 mg, 1.44 mmol) in tetrahydrofuran (4 mL) at 0° C. was treated with a 60% dispersion of sodium hydride in mineral oil (69.3 mg, 2.89 mmol) followed by iodomethane (225 mg, 1.59 mmol). After stirring at 0° C. for 0.5 h, the reaction mixture was allowed to warm to room temperature and was stirred at room temperature for 5 h. At this time, the resulting mixture was quenched with a saturated aqueous sodium bicarbonate solution. The reaction mixture was extracted with ethyl acetate. The combined organics were washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography (30% ethyl acetate/hexanes) afforded 4,6-dichloro-1-methyl-1H-pyrrolo[3,2-c]pyridine (278 mg, 95.8%). LC-MS calcd. for C8H6Cl2N2 [(M+H)+] 201, obsd. 200.8.

1. temperatureto warm to room temperature
2. stirringwas stirred at room temperature for 5 h
3. customAt this time, the resulting mixture was quenched with a saturated aqueous sodium bicarbonate solution
4. extractionThe reaction mixture was extracted with ethyl acetate
5. washThe combined organics were washed with a saturated aqueous sodium chloride solution
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-b6b9ce3b0306406d9845b643d2b95d14

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722661B2