Methyl iodide → 3-bromo-1-methyl-1H-Pyrrolo[3,2-b]pyridine

A mixture of 3-bromo-1H-pyrrolo[3,2-b]pyridine (450 mg) in DMF (5 mL) was treated with a NaH (60% in oil, 100 mg) and the resulting mixture stirred at room temperature for 5 min. The mixture was cooled to 0° C., treated with MeI (324 mg) then allowed to warm to room temperature over a period of 1 h. After this time, the reaction was diluted with water (100 mL) and extracted with AcOEt (3×50 mL). The combined organics were washed with water (50 mL), 5% LiCl aqueous solution (50 mL) then brine (50 mL), dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (heptane to AcOEt) to give the title compound (408 mg).

1. temperatureThe mixture was cooled to 0° C.
2. temperatureto warm to room temperature over a period of 1 h
3. extractionextracted with AcOEt (3×50 mL)
4. washThe combined organics were washed with water (50 mL), 5% LiCl aqueous solution (50 mL)
5. dry with materialbrine (50 mL), dried over Na2SO4
6. filtrationfiltered
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe residue obtained
9. customwas purified by silica gel column chromatography (heptane to AcOEt)

ORD record

ord-0ccae535d7694ee7a343d1fc214fdd8d

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029536B2