Methyl iodide → 6-Bromo-1,3,3-trimethyl-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one

Temperature

0 °C

In a 25-mL, round-bottomed, single-necked flask was placed 6-bromo-3,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-2(3H)-one (500 mg, 2.07 mmol) in DMF (5 mL). The mixture was cooled to 0° C. followed by an addition of NaH (60%, 99.55 mg, 2.49 mmol). The reaction mixture was stirred at 0° C. for 20 min. To this was added MeI (0.39 ml, 6.22 mmol) at 0° C. Then, it was slowly warmed to room temperature and stirred for 3 h. The reaction mixture was quenched with sat. NH4Cl (5 mL) and the organic layers were extracted with EtOAc (3×5 mL). The combined organic layers were washed with water (2×5 mL) and brine (1×5 mL), dried (Na2SO4), concentrated, and purified by flash chromatography (100% Hexane to 100% EtOAc) to give 455 mg (86%) of 6-bromo-1,3,3-trimethyl-1H-pyrrolo[3,2-b]pyridin-2(3H)-one.

1. customIn a 25-mL, round-bottomed, single-necked flask was placed
2. temperatureThen, it was slowly warmed to room temperature
3. stirringstirred for 3 h
4. customThe reaction mixture was quenched with sat. NH4Cl (5 mL)
5. extractionthe organic layers were extracted with EtOAc (3×5 mL)
6. washThe combined organic layers were washed with water (2×5 mL) and brine (1×5 mL)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated
9. custompurified by flash chromatography (100% Hexane to 100% EtOAc)

ORD record

ord-2f5d4316c1c644cdba5ca4dd9319c86a

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376441B2