Sodium hydride → HCID 123719240, compound

To dry NaH (360 mg, 15.0 mmol) under an Argon atmosphere was added dropwise a solution of compound 82a (1.92 g, 6.80 mmol; based on 85% purity) in anhydrous DMF (20 mL). After stirring at room temperature for 1 h, the mixture was cooled to 0° C. and 2-(trimethylsilyl)ethoxymethyl chloride (3.07 mL, 17.0 mmol) was added dropwise over 2 min. The mixture was stirred at room temperature for 1.5 h. The mixture was quenched carefully with 1 mL of saturated aqueous NH4Cl and poured into water (150 mL). After saturating the aqueous mixture with solid NaCl, the mixture was extracted with EtOAc (3×25 mL). The combined extracts were washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to give a pale brown solid which was purified by flash column chromatography on silica gel (0-40% EtOAc-heptane) to afford compound 82b as a white solid. Mass spectrum (LCMS, ESI pos.): Calcd. for C14H20BrN3O2Si, 392.1/3.94.1 (M+Na). found 392.2/3.94.1.

1. temperaturethe mixture was cooled to 0° C.
2. stirringThe mixture was stirred at room temperature for 1.5 h
3. customThe mixture was quenched carefully with 1 mL of saturated aqueous NH4Cl
4. additionpoured into water (150 mL)
5. concentrationAfter saturating the aqueous mixture with solid NaCl
6. extractionthe mixture was extracted with EtOAc (3×25 mL)
7. washThe combined extracts were washed with brine (50 mL)
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customto give a pale brown solid which
12. customwas purified by flash column chromatography on silica gel (0-40% EtOAc-heptane)

ORD record

ord-e55279e4ef7f43eb9daa7a5f5d77a8fe

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249163B2