Tetrahydrofuran → HCID 86723962, compound

6-chloro-1H-pyrrolo[3,2-c]pyridine (1 g, 6.6 mmol) was dissolved in DMF (5 mL) under Ar and the solution was cooled in an ice water bath. A 1 M solution of NaHMDS in THF (7.5 mL, 7.5 mmol) was added over 1.5 min and the reaction mixture was stirred 20 min. (2-(chloromethoxy)ethyl)trimethylsilane (1.3 mL, 7.5 mmol) was then added and the reaction mixture was stirred for 2 h. The mixture was then diluted with water and DCM, and the aqueous phase was extracted with DCM (2×). The combined organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated to afford a crude residue that was purified by silica gel chromatography (0-50% EtOAc in hexanes) to afford 6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,2-c]pyridine. LCMS-ESI+ (m/z): [M+H]+ calcd for C13H20ClN2OSi: 283.10; found: 283.03.

1. temperaturethe solution was cooled in an ice water bath
2. additionwas then added
3. extractionthe aqueous phase was extracted with DCM (2×)
4. washThe combined organic phase was washed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customto afford a crude residue that
9. customwas purified by silica gel chromatography (0-50% EtOAc in hexanes)

ORD record

ord-77ba809f09924732828d09df738b632d

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376441B2