Tetrahydrofuran → HCID 124025697, Verbindung

Temperatur

70 °C

To a solution of 3,3-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one (56 mg, 0.20 mmol) and 3-iodooxetane (85 μL, 0.98 mmol) in DMF (1 mL) was added a THF solution of NaHMDS (1.0 M, 0.21 mL, 0.21 mmol). After 1.5 h, the reaction mixture was heated to 70° C. After an additional 1.5 h, the reaction mixture was cooled to r.t. and additional 3-iodooxetane (30 μL, 0.34 mmol) and NaHMDS solution (0.1 mL, 0.1 mmol) were added. The reaction mixture was heated to 70° C. and was stirred an additional 16 h. The reaction mixture was cooled and diluted with EtOAc, water, and brine, and the layers were separated. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified by silica gel chromatography (0-50% EtOAc in hexanes) to provide 3,3-dimethyl-1-(oxetan-3-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one (7.43). LCMS-ESI+ (m/z): [M+H]+ calcd for C19H27BNO4: 344.20; found: 316.25.

1. waitAfter an additional 1.5 h
2. temperaturethe reaction mixture was cooled to r.t.
3. temperatureThe reaction mixture was heated to 70° C.
4. temperatureThe reaction mixture was cooled
5. customthe layers were separated
6. washThe organic phase was washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude residue was purified by silica gel chromatography (0-50% EtOAc in hexanes)

ORD-Eintrag

ord-a2bdf0fca5c94108bb56870e1feb231d

Quelldatensatz

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09376441B2