Iodoethane → HCID 86704559, compound

Temperature

0 °C

A solution of 4,6-dichloro-1H-pyrrolo[3,2-c]pyridine (250 mg, 1.34 mmol) in tetrahydrofuran (4 mL) at 0° C. was treated with a 60% dispersion of sodium hydride in mineral oil (64.2 mg, 2.67 mmol) followed by iodoethane (229 mg, 1.47 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 overnight. 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/hexane) afforded 4,6-dichloro-1-ethyl-1H-pyrrolo[3,2-c]pyridine (200 mg, 69.6%). LC-MS calcd. for C9H8Cl2N2 [(M)+] 214, obsd. 214.9.

1. temperatureto warm to room temperature
2. stirringwas stirred at room temperature overnight
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-b07ad3f65a454ad9bc6d621bbc25a9c6

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722661B2