Sodium hydride → HCID 123305347, compound

To dry NaH (67.8 mg, 2.83 mmol) under an Argon atmosphere was added a solution of compound 84b (532 mg, 1.88 mmol) in anhydrous DMF (5 mL) slowly over 2 min. The mixture was stirred at rt for 1 h and then cooled to 0° C. 2-(Trimethylsilyl)ethoxymethyl chloride (0.612 mL, 3.391 mmol) was added dropwise over 2 min. After stirring at rt for 1 h, the mixture was quenched carefully with 1 mL of saturated aqueous NH4Cl and poured into brine (75 mL). The mixture was extracted with EtOAc (3×25 mL) and the combined extracts were washed with water (2×25 mL) and brine (25 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to give a faintly yellow crystalline solid. The solid was purified by flash column chromatography on silica gel (0-40% EtOAc-heptane) to give compound 84c as a white solid. Mass spectrum (LCMS, ESI pos.): Calcd. for C14H20BrN3O2Si, 392.1/394.1 (M+Na). found 392.2/394.1.

1. temperaturecooled to 0° C
2. stirringAfter stirring at rt for 1 h
3. customthe mixture was quenched carefully with 1 mL of saturated aqueous NH4Cl
4. additionpoured into brine (75 mL)
5. extractionThe mixture was extracted with EtOAc (3×25 mL)
6. washthe combined extracts were washed with water (2×25 mL) and brine (25 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customto give a faintly yellow crystalline solid
11. customThe solid was purified by flash column chromatography on silica gel (0-40% EtOAc-heptane)

ORD record

ord-b9b317d40fdd485abadb66ffe4a43ea1

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249163B2